Is there a reason this isn't done as frequently?

The silver lining I suppose is you only lost $1000, this is a relatively cheap lesson in real estate, investors frequently lose more than that on bad flip projects. 

Federal, state, and city landlord-tenant laws change frequently.

Make sure the lenders you end up using are investors themselves or work with investors frequently.

If you have an agent you're planning to use as the buyer, I would ask them get this through a rep they frequently use. 

., as a frequent visitor.

Also, a pro can assist you with tax planning for future years.That is, unless you're deeply knowledgeable in the tax codes and its frequent changes.

The thought of having STRs in areas we frequent in the surrounding areas sounds like a dream.

Figuring that out is entirely on the person taking the loan but the total financial worth of a person can certainly include items which Rich Dad would call a liability and other things besides.Separate from lender needs personally I reevaluate my net worth frequently just to have an idea on whether its growing as my cash flow is also growing.

The systemic problem is all of these people telling or marketing that you can make it big if you have bad credit no cash no experience.. well this may be true for 1 out 10,000 but the rest are not going to make... even on BP there is a no money down book.. so even though no money down deals can happen they are no frequent at least not on quality assets.