I've seen this and it's the blind leading the blind.

You are right about the risk that comes with the holding period but in my opinion sometimes you have to take the risk and make sure the profit that you generate is higher than the costs that you paid by holding the deal for a specific amount of time.

This could be laborious as a one at a time deal.Not sure if this would work but you might be able to pay someone from Fivr to write a script that would do it automatically for you and generate a list based off of the multifamily addresses that you already have.   

We are literally next to a golf course and about 10 mins from a ski place and I don't think fancier amenities would generate a ton of ROI. 

These are not great investments and while the experience is not typical for Memphis, nothing I've read or seen should lead you to believe your experience will improve.  

This thought led me into studying about becoming financially free and building generational wealth.

I've read about Benjamin Graham and Warren Buffets approach to investing at large and it resonates with me more so than the crypto-generation. 

Our LTR lease is nearly 18 pages long, not including the additional riders for mold, radon, lead based paint, etc. 

You can learn to do this independently or get a rockstar REALTOR to lead the way.

Networking with local real estate meetups in Raleigh or surrounding areas could also help you find leads directly from other investors.