A couple of them don't have experience living in a house, and I'd like to find an easy way to educate them on the systems while also encouraging proper maintenance of the HVAC, wood laminate floors, countertops, etc.

.  :-)If this doesn't help, maybe me bumping this thread up will encourage someone wiser to answer. 

I'm also encouraging my mother, father (both nearing retirement age) and "investor-minded" friends to do the same.

Thanks for the encouragement Katrina- I think I've had it drilled into my head from all of the salesmen out there that I NEED to start out wholesaling but I'm realizing from stories like yours, and others who have reached out to me since I posted this, that that is not the only way to go about it.

Do you use airbnb & vrbo, or any other platform for listing? 

You will be prolly buying in a different platform and price range, as to not be in competition with one another.

Community 2nds are down payments assistance programs that are backed by a community program that is designed to encourage home ownership among lower income people.

It's another smart, easy, convenient service through airbnb platform connecting hosts.

In that regard, it's encouraging to pore over the forums and witness just how supportive this community is towards those, like myself, who are just starting out.My wife and I will be moving to Richmond, VA within the next couple of weeks and are hoping to make our first investment a "house hack." 

My point is look at different listing  platforms.