If this is the case generally you would report your flip activity on Schedule C of your 1040 and any net taxable income from the flips would be subject to self-employment taxes on Schedule SE.Encourage you to work with a tax CPA/EA this upcoming year if you aren't comfortable DIY.

There are significant tax differences between the taxation of a pass-through entity and a C-Corp/S-Corp.Accountants would need all the detail(nature of business activities, goals, exit opportunities, income levels, expected income levels, etc) before they can make a well informed decision on your entity structure.Working as an independent contractor does have it's downsides of which you are paid the full-lump sum for your work.

I've been active in both markets since 2010.

It's not investing, it's active income and it's hard work.

As far as I can tell, from calls to Campus Life to asking the local REIA, there's no Off-Campus Housing info site at this college, no active roommate or rental housing listing on Facebook or Instagram.Has anybody ever started a Facebook group specifically for local student rental listings?

ADR and Occupancy rates are more of an art than a science, but using sites like AirDNA are great places to start and then verify thru local property management or just good old fashioned research on Airbnb and VRBO for active rentals in the area.  

It's a combination of number of posts, number of votes for those posts, and weighted differently for threads started vs comments on other people's threads.And it only looks at the last few weeks of activity, which is why some people with fewer posts and votes show up.

I am active duty enlisted Air Force, e4 making 3200ish a month.

A lot of it will depend on what business activities you will do, i.e. buy and hold rentals vs. flipping.

Look into taking advantage of the Military Tuition Assistance Program while you are on Active Duty.