I would like to point out that there are few soldiers who actually have to pay their own equipment.

But, I would think that if your Pistoleer is not an official part of an army (I.e. he has a Merc status) he is responsible for his own gear in which case he would probably have to pay it back (a loan) or he stole it and is probably wanted as a petty criminal.

I think you can easily compare him with a Samurai: if he is no noble he is not allowed to carry a Katana, if is is carrying one he got it from his Daimyo. When he has proven his worth to his lord the weapon is considered his and can be inherited in his family. Whe his lord has died before that, he is a Ronin, the weapon is still his but he can no longer pay for its upkeep, hence poor quality.

There are so many interesting ways to deal with this.