The only challenge I could see would be how you demonstrate your intent to hold for productive investment use. 

However, this strategy has been used successfully (without IRS challenge) by numerous property owners for nearly 20 years, including many public companies that have reported their transactions to the SEC, with the full acquiescence of their boards and outside auditors.

I spend a ton of time in Charleston and bought one park that I demo'd and built new construction on.. just a lot of moving pieces to make these things work this way.. and I guess if you have the net work right then what the heck.I don't work with wholesalers at all so not any thing I am interested in comparing.. to me its like the used car side of real estate.. no time for it or desire to engage those folks.

I understand you have to spend money to make money sometimes, but it can be a big challenge while going through a divorce. 

Off-the-rack advice might work, but it does more harm than good often enough that I no longer engage in it.Absent any other information I would be planning for you to need money for another 30+ years.

A few questions:1) what challenges have you experienced?

Been doing tons of research and it seems like New York can be a challenging area to getter started in as a newbie.

Since you are evaluating multiple out of state locations, this may be more challenging, but I bet you could find some folks here in the forums who can point you in the right direction. 

Single family properties are a challenge to crack into but most investors have been focused on secondary suites and diversifying their risk. 

Finding properties where the #'s would work of a sandwich lease and still be attractive to the seller, seems challenging.