The in-laws want simplicity since they have no interest in managing the unit.From what I understand, it seems logical for them to handle the required taxes (TAT & GET) and compensate me via a 1099 form.

Simultaneously, although I underwrite for long-term and that is the fall back, I generally do not have plans to keep long-term because I'm trying to grow differently than you are.Here are a few real examples and I will try to explain the logic.

This is obviously very costly and cumbersome for a property manager and Logical Property Management will not do it.

Do what you understand, what seems logical, and having construction knowledge is a massive advantage in my opinion. 

You would make $50K-$100K wholesale deals like we are doing.People hear what they want to hear.You answer logic and common sense, they won't have it.

If you are most concerned with time, I'd consider dropping your price to $1200 a month where this unit presents more of a value proposition, and will likely draw in a bigger pool of candidates for you to screen and find that best one.I'm happy to dive into the above further and explain my logic. 

I am about to make an offer on this Duplex and would appreciate if you guys could double check my logic and point out anything I may have missed.

I learned that sometimes when you feel something in your gut or spirit that does not sit right go with that over logic.

@Trey Watson, I need to educate myself on wholesaling before I can make any logical decisions on the topic. 

Courthouse steps deals are also typically cash only, with Cashiers Checks either paid on the spot, or if not within 24 to 48 hours of the auction.These are definitely both viable strategies, but with the amount of cash you have available Househacking a multifamily property, or a single family with an ADU, would be a more logical first step.