You’re spending a couple, hundred a year for a check that’s a couple hundred thousand higher plus you get to keep the rental income that you’d lose with the lower insurance and into rebuilding?

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.

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