Regardless of the asset class, the common thread is clarity, consistency, and respect.At Robin Hood Properties, we’ve learned that balancing profit with a deep commitment to customer satisfaction creates sustainable success for everyone involved.

If you have equity and decent credit, a conventional Fannie Mae HomeStyle (or the Freddie Mac version) would likely be the better option instead of an FHA 203k loan (which will require a 3rd party HUD consultant to oversee the deal in addition to having the contractor involved). 

Lots of time involved and educating the seller why to do this for you..  95% of sellers if they ask their attorney for advice will be given advice do not do this.

There is no seasoning requirement involved since the property isn't a short sale and it isn't someone buying REO from a bank with a seasoning requirement.

Be very careful who you take advice from online, you should get involved with a local attorney and a local realtor.

Real estate is transactional where people are involved so it won't be a black and white answer.The best to do is to find an agent that fits your needs and guide you through the process.

That’s the best bet.

I am also involved in management at one of the largest STR property management firms in Cashiers.

You mention not a fan of landlording, great, the bank never get's involved in that stuff right. 

Continually communicate clearly with all parties involved to make sure that expectations are as close to realistic timelines as possible.