He’d likely play the role of buyer’s agent, contractor, and rental listing agent—something we successfully did last June.

It will just be a lot of work to find experienced flippers playing in that price point

The benefits of Kissimmee for a newbie is analyzing property potential is very easy - you will have a ton of carbon-copy comps to look at and the online estimators like Airdna can actually be pretty accurate. 

I can provide him with an online log in so he can review the books from his office.

Thanks so much for posting all this info I had been looking at Apke Land or Land Investing Online, while they give lots of free information if you really want in depth or access to their letters you have to buy their course.

Appreciation in most Sec8 neighborhoods is very low so it’s a cash flow play.- I would highly suggest you plan on using a property management company.

But, if the deal is a true ABL play, I may not even look at a credit report at all.

Vrbo and Airbnb do not play around when they see you taking direct bookings from guests who found you through their platforms. 

Documenting your journey online or engaging on LinkedIn can also help expand your network.

Sometimes the best investment is found in a 'transitioning' market that is just outside the 'great' market and is in play to be the next great one.