It'd be helpful to know what you're looking to accomplish with a system as that dictates choice of which one to go with as they are all a little different. 

You will probably get others saying the same thing, and I ask this because I'm sure you have considered it but ultimately decided not to.

He has a knack for making bad choices. 

Quote from @Collin Hays: I suspect that the Smokies is your best choice, simply because it is a year-round destination. 

Hey Steven - An LLC is a solid choice for structuring your partnership since it offers liability protection and keeps things clean when splitting ownership and profits.

In absolutely no way would I ever depend on such a broad analysis to ultimately determine my decision.

I know there is a lot that I'm going to need to learn, and ultimately it will come down to how much the student puts into it.  

At the beginning, it may be difficult to get a more expensive property that will appreciate well and so your choice is go with the cheaper property and get cash flow until you can sell and upgrade, or wait for a really good deal which you may be waiting for quite a while and its possible that you will have spent so much time waiting that you could have purchased multiple cash flowing properties by the time you get a good appreciation deal that you can qualify for / refinance after the rehab. i know anyone can go out and get seller financing deals, HML, flip to build capital or whatever the case may be I am just saying sometimes those will be harder and could result in less deals overall. 

I have personally seen that scenario take place and what ultimately happened was that the company just came back to the debtor and said, "You have to come up with $XXX,XXX for us to be able to qualify you for help.  

Hiring a good property manager may cost more upfront, but it’s often the better long-term choice, especially if you want to avoid burnout or costly mistakes.Happy to dive deeper into any of these points if it helps!