A little about myself, I spent 11 years in the Army flying attack helicopters and now have a fulfilling job as a Medical Helicopter Pilot which gives me a lot of down time to spend on real estate investing.

You are wasting your time travelling to units anyway.

My plumber in the Triangle doesn't want to travel to Greensboro for smaller fix-its, and I have two smaller repair jobs. 

A legal structure can serve you(and your partners) for the long-term, so knowing where you want to travel plays a big role in deciding what path is right for you. 

my biggest fear is that my #1 plan is to go to medical school in which I will have pretty much be like $300kish in debt at the end of it and will have absolutely no income for 4 years.

I’ve made 6 figures consistently the past few years but I’ve spent most of it on high rent, leisure & travel to be honest so only have about 40k liquid for a conventional downpayment on a 200k property.

Once we achieve financial independence, I would love to travel the world, work as a freelancer if needed and spend time with family and work on my hobbies.

It will be interesting to see not only on-campus transformation, but also how off-campus medical office space evolves in the West End, Beacon Hill and Government Center.https://www.bizjournals.com/boston/news/2019/05/13/first-look-mgh-plans-1-million-square-foot.html?

And let's face it: no one is saying "let's travel to DFW for a nice vacation".

I get to travel for work, and really enjoy my job.