I also know I can look at ways of borrowing against that equity (HELOC for example) but I also just feel like if I take debt on that property the cashflow goes down, and then if the association also takes the loan it goes down more, and at that point I don't know why it would be a better option than selling before August. 

Hey @Sundone Boutvyseth,Similar to what @Brad Jacobson said, your best option might be a secondary residence loan if you want to STR.

I would start there and think of anything that I could do to stay in the house for a while as it sounds like you would be losing a bit of money with the other options. 

VRBO of course has no co-hosting option.

My area is relatively low crime, but had one place that someone broke a window to get in.... probably a homeless guy looking for a place to sleep....got scared when neighbor turned light on.I put in a SimpliSafe unit... portable, easy to set up, multiple options- you can use a webcam and get alerts on your phone and future tenant can pay for full service if they want. 

If you're considering Real Estate as an option in the future, I would not add the money to either of these accounts. 

There are many other options as well including some that are included in property management software products. 

With the right resources and help, you can still make it happen.There are options that can help make buying a home possible today — even if your savings are limited or your credit isn’t perfect.

OC California is very expensive so investing out of state can be a good option.

I know it is an especially difficult market to break into as a new investor due to demand and competition, but I feel that it is still my best option.