So, the following comes from the perspective of a small-portfolio landlord who is a DIYer who lives close to his units and doesn't want to pay for a Registered Agent and PO BOX.

We still live in the home I purchased however I will sell it once we decide to move.

Buy a duplex or small multi family, live in one unit and rent the rest.

I STILL live at home and my parents are urging me to get out of the house but I don’t want to make a big financial mistake and purchase something out of emotion.

From my understanding, your child could buy property/ hold mortgage for you to live in.

Many in single LLC though do it in a way to make their lives simple, For Example 123 Main St LLC  etc.

This would be to get an idea of the layout of the bedrooms/bathrooms and other living spaces.5.  

I live in South Florida and it's basically cooked down here so I have been scouring my state and found fairly promising properties under or around 250k but it's 5 hours away from where I live?!

If you're using regression to predict how much a market would appreciate by I think that would be a much easier regression task then predicting how inflation would increase the price of a gut rehab (increased parts and labor prices due to increased cost of manufacturing and increased cost of living respectively). 

Unless you live there and are up for it, you’re going to need to find a great property manager.