Dante's financial life when it's brought up is usually depicted as either alright, to downright deplorable. His office seems to double as his home since he sleeps, bathes, and hangs out there most of the time. However, one can assume that devil hunting doesn't exactly make bread in the Devil May Cry universe and this creates some financial troubles for Dante's business.
(Keep in mind that each game's office was made by a different team for each game, so they all look different from one another.)
DmC
So Dante's place is DmC used to be a luxurious mansion that was wide acres of lush forest and monumentally rich. However, after the attack, the home has been left in shambles and rots from time and Limbo's influence. After the events and other situations, Dante is resigned to live in a trailer.
It appears to me that New!Dante might have other ways of making money to keep his trailer with power. I could assume he works odd jobs at the carnival he's stationed in like cleaning up trash or working some of the rides. Since the carnival seems to be the type to hire anyone as long as they work, the owner probably doesn't mind Dante's strange lifestyle (or doesn't know about it) and since Dante being called a terrorist didn't start until later on in the game, he was probably considered some normal street punk who just needed a place to stay. Of course, this was all thrown away once the hunter demon came and destroyed his home. Then things went on with Limbo, his brother, and killing Mundus. Finally, after fighting Vergil, he is left with Kat to fight off the rest of the demons in the world. I could assume that Dante and Kat will try to fix up his old home and make it a living arrangement for the time being.
DMC3
Dante's office here is more or less a new office that had been bought by Enzo for Dante and therefore was the one paying for it in order to keep the lights and water on. If we take the manga into consideration, Enzo was sick of having to keep up with the payments and was ready to give up on it. But Dante decided to keep it and it was probably on its last leg of electricity and utilities before the city cut it off. However, then the demon invasion and Temi-ni-gru rose up and things probably changed. After everything that happened, Dante fixed it, and it probably had some electricity going until the time prior to DMC1. Not only that, but he also seems to owe Lady money not only for her motorcycle but with other things that probably have to do with keeping the lights on in his office.
DMC1
By the time of Devil May Cry 1, much of Dante's life of Demon hunting has thrived at the beginning, but as time went on, Dante's financial gain hasn't seemed to get him much jobs. As we see in the beginning of DMC1, Dante comments on not getting anywhere with his gig of demon hunting like he wanted. This seems to be the start of his issues, along with owing Lady money that he probably borrows for pizza or paying for his office. of course, begins the entrance of Trish, the battle against Mundus and Trish joining Dante in Devil May Cry, or renamed "Devils Never Cry". It can be assumed that she helped pay for Dante's office by accepting some of the gigs that he doesn't want to do. Then Trish left and Dante changed the office name back to Devil May Cry, thus beginning his struggles.
DMC: anime
The anime is where I feel the whole "Dante is poor" trope came from. As @berto also said; The anime depicted Dante as a "barely struggling" gun-for-hire. His office is usually dark, dingy, and not very well kept. There is a lot of expensive furniture and things in it, but I notice that it doesn't seem to have lights on. It's always dark with only a small source of light on that's probably from a battery-powered light. I'd wager that Devil Hunting doesn't pay as much as needed to keep up an office's electric bill. That or Dante doesn't take many jobs and that's one of the reasons he's in the situation he's in. Then if you add the money he seems to owe Lady, the amount of money her and Trish spend while sending him the bill, Patty now staying there as well, it's any wonder how Dante even keeps up with the office.
DMC4
By this time, it can be assumed that Dante is doing much better then he started off. We can see that by Trish seemingly returning to working with him, and Lady coming around more often to give him some jobs to work. These jobs seem to be where most of his income originates from. Because of this, Dante is now able to keep the lights on, and afford to pay what he owes Lady. It also allowed him to buy some new clothes (as ridiculous as they look) to go hunting. I'd say this is the point where Dante was doing his best.
DMC2
In DMC2, we don't really see much of his office, but we can assume that it's gone through a bit of renovations compared to the past (obviously due to different people making the office for each game) but it definitely looks the cleanest his office has ever been since probably DMC3.
DMC5
and thus us coming to DMC5 where we're further shown how Dante is doing. It can be assumed that he's slowing following to hard times do to the lights barely being on, his comment on how "the water needs turning on and those toilets need flushing," and even his choice in attire.
Rather then all that leather, and dressing in a more detective-style as he did in DMC1, or even the full on Devil hunter get up in DMC2, he seems to have fallen towards more conventional clothing of boots, leathery pants, a long-sleeved shirt, and a duster that could probably be found at a thrift shop. All-in-all Dante has not been doing so hot in the events of DMC2 to DMC5. This is also evident in how he quickly accepted the job Morrison gave him once 'cash up front' was on the table.
So based on all the games we've seen Dante in, his financial struggles have been present and alive depending on the time in Dante's life you wanna look at. I would say DMC4 was around the time where he was doing well, then after DMC2, things fell on hard times again.
(Keep in mind that each game's office was made by a different team for each game, so they all look different from one another.)
DmC
So Dante's place is DmC used to be a luxurious mansion that was wide acres of lush forest and monumentally rich. However, after the attack, the home has been left in shambles and rots from time and Limbo's influence. After the events and other situations, Dante is resigned to live in a trailer.
It appears to me that New!Dante might have other ways of making money to keep his trailer with power. I could assume he works odd jobs at the carnival he's stationed in like cleaning up trash or working some of the rides. Since the carnival seems to be the type to hire anyone as long as they work, the owner probably doesn't mind Dante's strange lifestyle (or doesn't know about it) and since Dante being called a terrorist didn't start until later on in the game, he was probably considered some normal street punk who just needed a place to stay. Of course, this was all thrown away once the hunter demon came and destroyed his home. Then things went on with Limbo, his brother, and killing Mundus. Finally, after fighting Vergil, he is left with Kat to fight off the rest of the demons in the world. I could assume that Dante and Kat will try to fix up his old home and make it a living arrangement for the time being.
DMC3
Dante's office here is more or less a new office that had been bought by Enzo for Dante and therefore was the one paying for it in order to keep the lights and water on. If we take the manga into consideration, Enzo was sick of having to keep up with the payments and was ready to give up on it. But Dante decided to keep it and it was probably on its last leg of electricity and utilities before the city cut it off. However, then the demon invasion and Temi-ni-gru rose up and things probably changed. After everything that happened, Dante fixed it, and it probably had some electricity going until the time prior to DMC1. Not only that, but he also seems to owe Lady money not only for her motorcycle but with other things that probably have to do with keeping the lights on in his office.
DMC1
By the time of Devil May Cry 1, much of Dante's life of Demon hunting has thrived at the beginning, but as time went on, Dante's financial gain hasn't seemed to get him much jobs. As we see in the beginning of DMC1, Dante comments on not getting anywhere with his gig of demon hunting like he wanted. This seems to be the start of his issues, along with owing Lady money that he probably borrows for pizza or paying for his office. of course, begins the entrance of Trish, the battle against Mundus and Trish joining Dante in Devil May Cry, or renamed "Devils Never Cry". It can be assumed that she helped pay for Dante's office by accepting some of the gigs that he doesn't want to do. Then Trish left and Dante changed the office name back to Devil May Cry, thus beginning his struggles.
DMC: anime
The anime is where I feel the whole "Dante is poor" trope came from. As @berto also said; The anime depicted Dante as a "barely struggling" gun-for-hire. His office is usually dark, dingy, and not very well kept. There is a lot of expensive furniture and things in it, but I notice that it doesn't seem to have lights on. It's always dark with only a small source of light on that's probably from a battery-powered light. I'd wager that Devil Hunting doesn't pay as much as needed to keep up an office's electric bill. That or Dante doesn't take many jobs and that's one of the reasons he's in the situation he's in. Then if you add the money he seems to owe Lady, the amount of money her and Trish spend while sending him the bill, Patty now staying there as well, it's any wonder how Dante even keeps up with the office.
DMC4
By this time, it can be assumed that Dante is doing much better then he started off. We can see that by Trish seemingly returning to working with him, and Lady coming around more often to give him some jobs to work. These jobs seem to be where most of his income originates from. Because of this, Dante is now able to keep the lights on, and afford to pay what he owes Lady. It also allowed him to buy some new clothes (as ridiculous as they look) to go hunting. I'd say this is the point where Dante was doing his best.
DMC2
In DMC2, we don't really see much of his office, but we can assume that it's gone through a bit of renovations compared to the past (obviously due to different people making the office for each game) but it definitely looks the cleanest his office has ever been since probably DMC3.
DMC5
and thus us coming to DMC5 where we're further shown how Dante is doing. It can be assumed that he's slowing following to hard times do to the lights barely being on, his comment on how "the water needs turning on and those toilets need flushing," and even his choice in attire.
Rather then all that leather, and dressing in a more detective-style as he did in DMC1, or even the full on Devil hunter get up in DMC2, he seems to have fallen towards more conventional clothing of boots, leathery pants, a long-sleeved shirt, and a duster that could probably be found at a thrift shop. All-in-all Dante has not been doing so hot in the events of DMC2 to DMC5. This is also evident in how he quickly accepted the job Morrison gave him once 'cash up front' was on the table.
So based on all the games we've seen Dante in, his financial struggles have been present and alive depending on the time in Dante's life you wanna look at. I would say DMC4 was around the time where he was doing well, then after DMC2, things fell on hard times again.
