To me this sounds like a heads they win tails they lose proposition.  

I'm worried if I do it I wouldn't get the property booked enough and end up losing money.

Appraisal Contingency - This is the reason you're losing out to cash buyers.

Anything related to tenants requires a real estate professional that has a license to lose if they screwup!!!

Anytime an HOA is involved, you are going to lose most times.

On my first deal, I hoped I didn't lose money. 

Agreed.While some HOA's are cool, you are pretty much handing over your money to lose some of your options.

It is prudent for the seller to know enough about the market to properly analyze the improvements and their effect on the value of the property.From the buyers side, only put down an earnest money deposit that you can afford to lose.

As a person with extensive use experience of such, I will say at worst would take maybe as much as 1hr to track an heir, emphasis on "an" as the correct tool in this arena, or more specifically the one I used, I could dig up the last 30 years of a persons history, every address, co-habitant, everyone in 1 degree of separation, there 30yr residency/ work. sphere and so on and so fourth. 

And that is buy the property as agreed upon “as-is” or lose the earnest money.