@Pedro TorresWelcome to BP.I recommend connecting with a property manager in the area to get the full scoop in terms of market rents and vacancy rates.

We have a couple of guys that do it but trysting that they have done a full winterization correctly is another matter. 

I complete the full house sale contract with the addendum, and take a substantial earnest money.I include that the earnest money is non-refundable in the event that the lease expires.

It is now producing great cash flow, and it should gross around 32-35k on the full first year.Lessons learned?

Owner can’t afford the full rehab. 

Or if they are, your purchase & sale agreement should stipulate that any outstanding liens, taxes, fines or fees will be paid in full by the seller at closing.Be sure you're working with a full-time Realtor and you should be OK.Let me know if you have other questions.

I am guessing that I can't use the proceeds to "buy/pay off" properties acquired in full through tax deed sale (past redemption) by an entity controlled by me into my own family trust either?

That’s what it’s for...your full financials for taxes, investors, etc. 

You're planning to pay full price, which doesn't give you a lot of headroom.Worst of all, as an investment, this is only showing a 5% cash-on-cash return.Why don't you look into a multi-family?

His plan will is to obtain delayed financing ASAP after purchase so he can pay me back in full w/in 1-2 months.