In 2000, a rule was approved for a Homeownership Voucher Program to allow recipients of Housing Choice Vouchers to instead receive assistance with a mortgage and other homeownership costs.

I know how to pull comps, access to MLS and all that good stuff however this is not sufficient to me. 

No telling if unpaid materiel liens will show up.Assuming you can sell it for $250,000 there won't be much if any profit.Consider this a learning experience and use the what you have learned to make better choices in the future.Let us know what happens.Good luck.

@Carolyn Morales, sounds like triplex is the right choice from a zoning standpoint. 

If she is month to month you always have the choice not to reextend their lease.

My question is what is the better choice to use those funds towards...flipping a SFH or buying duplexes or waiting until another market crash and wait to buy multiple investments?

MORE CHOICES...more money, more ideas, more opportunities.

Does someone have to send out a 1099 / 1098 or can we be self sufficient?

I recently acquired (not completely by choice) a rental which is next door to an uninhabitable house in a semi-rural area out-of-state.

If you hijack the GC built in profit then most of the time the  GC will have no choice but walk away.