I'm on standby to assist with Property Management, no risk to give us a try!

The other factor that's relevant for me is that my husband is a high end W-2 wage earner and we could greatly benefit from the potential tax benefits of actively managing the property. 

I think that areas on the outskirts of desirable cities where many people are moving (ie: Charleston) have great long term potential, as eventually people start to rent right outside the downtown area when prices rise. 

The best strategy is to not quit your day job until you've built a portfolio big enough meet your income requirements.You have three potential paths.  1) Build an active investing business, something that takes time.

Are there any potential flaws in the way we are setting this up?

The buyer makes payments to you, and you continue paying your original lender, profiting off the interest rate spread.However, this does come with risks, mainly the due-on-sale clause, which allows the lender to call the loan due upon transfer.

November to March tends to be the slowest leasing period so you are likely fighting that battle, but if you aren't at least beginning to receive more inquiries or having showings without tenants at minimum interested in a mid March/April move-in there are two potential issues: the home is over priced compared to competition or the property is inferior in condition.

I hear this even in popular podcasts like Thanks for Visiting where they recently have been interviewing very seasoned, successful MTR hosts and keep asking 'but what about the risk of squatters??'

And you now own real estate that will hopefully appreciate and when you move out will potentially provide cash flow. 

He has a few potential buyers going out to see it soon so I'm hoping someone he can find a buyer for it.