Although there are many issues and questions for you to knock out, the underlying question is to build or buy.Building or developing, you have two profit streams. 

Remember, no system is perfect, so avoid the temptation of constantly chasing after the next shiny object.

Can you have a business where you constantly make 40K flipping houses?  

As a commercial operation I had to keep a log of maintenance and was constantly worried about state inspections because a lot of the time we really weren’t in operation but for the state inspectors you were supposed to be available from 8am-5pm everyday of the season.

I'd rather just pay the slight premium to get into the bigger market, personally.Anecdotally, the STR Facebook groups I'm in are constantly full of posts with people in the Georgia mountains panicking about empty calendars. 

To me the quadplex would be dual purpose, while you are not living there it serves as a reliable stream of income, once you move there, you could live in 1 of the units while you build your permanent home, and you could also use it for when your family comes over for large gatherings.A 2nd option might be to build an RV park, Unless their are zoning restrictions, you should be able to build one fairly inexpensive, with a septic system and either public water or a well, you can keep your costs to a minimum by doing gravel roads, which are easier to remove later if you don't want them. 

I’m diving headfirst into learning everything I can to become fluent and knowledgeable in this field.What really excites me about REI is the hustle—the constant growth, challenges, and opportunities that come with it.

Constantly thinking the pros and cons of each and it has me stuck.

As you may know, a good portion of your monthly rent will not go in your pocket, it will go to the constant maintenance, upkeep, repairs, taxes and the like.Fourth, ask yourself... if you have a vacancy, the economy goes in the tank, you have huge unexpected repairs, etc....will your tenants chip in to help you out?

Remember, no system is perfect, so avoid the temptation of constantly chasing after the next shiny object.