Does anyone have any experience of getting into real estate this way?

Talking DOM is a 'blah, blah, blah' experience with landlords. 

My experience is that when people can afford to keep their expensive property, (sans a house), they rebuild.

In addition, I've helped many other investors finance their deals as a mortgage broker.I'm happy to share my experience as both an investor and lender.

It depends. all you talked about was the property but financing is more about the borrower, their experience, their credit, the cash available etc.

He has been saving his money for years and has plenty of money saved but no experience with real estate investing.

Sounds like for now the idea of eventually selling the branded account is a no-go, but there still remains pros/cons on each option and I'd love to hear what others have considered or their experience in adding more STRs/boutique hotel type properties to their portfolios.

If you have any experience with real estate in the greater Charleston area, I’d greatly appreciate your feedback and insights.

Glad to share my experience in OH too if anyone is interested. 

We can also lend to both individuals and LLCs.I'd be happy to share my experience as both an investor and as a lender.