As I mentioned, the condo association docs don't prohibit it, but they still may try to block it and get lawyers involved.

As mentioned, I don't have much to offer in terms of real estate experience but I can certainly keep you in great coffee and humorous travel anecdotes for your time if that means anything.  

I saw criteria for this before that mentioned you can't have lower pricing on another platform than on HA/VRBO, not sure if this is still criteria.Thoughts?

@Jay HinrichsAlways feel honored when mentioned by name from you.

Every no brings you closer to a yes.With a limited track record you could get a partner on a deal, wholesale a deal until you have enough money to have a bigger deposit, or like @Peter Sanchez and @Alexander Felice mentioned house hacking.Real estate is amazing because you have unlimited options and have to develop the mindset that you are a real estate transactor.Let me know if you need help with anything and I would be happy to help!

As the previous poster mentions a flip without any experience may be a bit tougher. 

I do collect applications on paper tho, for the reasons mentioned above and just send screened applicants the link for the background report.

After he missed rent he mentioned he just got a new job and would pay, after a week, he stopped answering my calls so I went to the property. 

Yes, i forgot to mention that, i plan on having all units leased before refinancing.  

You didn't mention your other bills, like credit card debt, car payment, child care, etc so I'm assuming they are easily payable or nonexistent.