I'd say have a big store clean first, it's amazing how much crap you can collect. All it does it sit there anyway so just get rid of it.
Well as you say $100 don't go far, I only feel entertained hunting big mobs these days so I'm looking at $300+ deposit probably. Admittedly I have a withdrawal being proceeded for the sale of my MF chips which I deposited for originally. So my mind will feel a lot more comfortable once that is put to bed.
Then I'll try a depo after (that could be 3 months out of game for me), regardless what some say I think a depo makes a difference with returns.
You have to way up your personal costs with what you're willing to contribute to the game on a monthly basis, if the balance isn't right for you then you need a rethink.
If you're chasing it though, that's just going to piss you off even more if it goes wrong, and you're be in an even deeper hole that you're unhappy with.
So free up peds first in game, even if it means going to the basic one set of armour and one gun, and nothing else first. At least that gives you another chance without depo.
Good luck
Rick