The mortgage is currently under my name, so I’m unsure what benefits, if any, I’d gain from using an LLC in this situation.

And if you convert it to a rental you’ll be facing a $200k taxable gain. 

At the same time, my market appreciates well so I gain significant value by holding on for the long-term.

You have to see huge appreciation to see any gain. 

As you gain experience and tackle even bigger projects, you'll realize that what once seemed like a mammoth deal becomes totally doable.When it's crunch time, there is no room for improvisation.

Brady,When I do my screening for new tenants I would weight the rental history the most.  

Being a curious person, I gained an interest in real estate investing due to other classmates being interested in real estate.

These companies, run by Kevin Bupp, Brian Spears, and Joanna Bupp, and how they buy up "mom & pop" mobile home parks, jack the rents up immediately to gain the most profit in the shortest amount of time with no care of the low income, fixed income, and elderly that were living in the mobile home parks comfortably.https://www.wivb.com/news/investigates/akron-mobile-home-residents-fight-back-against-out-of-town-owner/1779504663  That's how life works.

There is realized gains & profits, and UN-realized gains and profits.

While I haven’t chosen a specific niche yet, I’m leaning toward purchasing a multi-unit apartment where my 20-year-old son could live and help manage while we rent out the other units—essentially a form of house-hacking.So far, I’ve connected with a few real estate agents and gained MLS access, which has been a great starting point.