For those ones maybe charge $250 for cleaning, and if they want you to replenish everything such as paper towels, TP, soap, laundry detergent, coffee, etc., do it for the full $300. 

Also not to mention they know the drill, I don't have to explain much at all and off we go.The problem I'm running into is when I run out of money it's difficult to sell the loan to replenish the money supply.  

HELOCs, aren't necessarily risky either but they come with a few extra variables, adjustable rates, draw and pay-back periods, some come with early payoff fees...but they can be replenished and re-used over and over during the draw period so that might tilt the scale for you.

Now they're going to keep the increase in place to replenish the fund they pulled from.

You may need a source of funds in a worst-case scenario, just to carry you until you are able to replenish reserves.

Use your savings, then replenish with the gift/loan?

if i were already loaning them one of my houses, i'd be skeptical to act as their bank and loan them money as well, albeit out of their own security deposit.but that said, i am holding their SD in good faith so yea if its legal i'd do as u say and loan them $ out of their SD to bring their gas bill current but require it to be replenished over affordable installments paid starting ASAP meanwhile yea the gas co monthly plan helps defer the total due, right? 

This should come out of his security deposit, he should be required to make up any difference, and then he should be required to replenish the security deposit immediately.

Next, while it's a good idea to have reserves and I don't know the rest of your financial situation (ie how much disposable income you have left over each month), you said without the car payment you would be able to save up quickly.What if you kept the car, bought the property with the reserves in the bank with very little out of pocket (shouldn't be too hard with 100% financing and credits for closing costs), then paid off the car loan with your cash, and then quickly replenish your reserves?  

I feel you should have enough to cover your most expensive cost, usually replacing a roof. if you save up enough for a new roof then chances are you will have enough to cover any expenses that come up. just make sure to replenish that capex money once you use some of it, this way it is always there in case you need it.