For example, a light documentation program would require less debt-to-coverage ratio, but the rates would be higher (7-10 right now).

Fortunately, I'm lucky enough to have family members who are willing to lend me the additional funds to kickstart my investment journey.

I prefer SayRhino.com but would like a company that offers many other choices like LeasyEasy or others in addition.   

In addition, master policies are increasing for condos which increases the amounts of the association.

One additional note is that this cannot be financed through a conventional loan nor can it be used as a short term rental because I would be purchasing the building on the land owned by the association, which I'd have partial ownership of.I am considering offering $240K cash, or a lease option, with the following terms.7 year lease @ $1K/month with the option to purchase at $225K at the end of the lease. 

Additionally, I have founded and operated my own small businesses in the past. 

Would need to know a bit more about your situation, but we have done something to help investors modify their debt service on portfolios.  

You may want to see if you can claim real estate professional status now or sometime in the future based on your participation within real estate of being a landlord in addition to being an agent.You may want to have your past couple of returns looked at for review to see if they were done correctly.

I’d probably lean selling in that case, h st which that area prices really revolve around is in rough shape, and in addition you kind of end up competing against the massive amount of new apartments/condo’s on the h st/noma/union market area, it’s possible it increases in price but 1031ing that into a Property in pg county or something seems like a much easier play/bet

These might include creating an emergency fund, paying off debt, saving for a home, or investing for retirement.Prioritize the creation of an emergency fund.