The bigger concern is that between ALL the ways in which they take a bite, their bite was about 20% of the rent. 

I have done this method in the past and seems to work just fine in most situations.

I would recommend thinking through what your concerns may be and create a list of questions to ask each property management company you speak with.

I'm happy to invest in improvement, but concerned about fundamental issues with the buildings that may be more difficult to address. 

If I can't find better alternatives I can always swallow my concerns and live with it at least for the first 3-5 years.

I'm a veteran as well and use the BRRRR method (out of state), it's EASY.

I just started with buildium it’s ok so far but my big concern it’s all cloud based which is good and bad, do I own that data are only own it if I keep paying?

If your goal is to maximize your retirement plan contributions with a SEP, then keeping things as a basic LLC might be better.If you're really concerned about keeping your brokerage and your personal commissions separate, then two separate entities, possibly either 2 S-Corps or a nested S-Corp/LLC structure might be best.So when tax season is over, sit down with your CPA and outline your goals and your issues and see what they recommend.Now if what you've got is a data entry/"tax preparer" who simply enters your data into tax forms, consider switching providers. 

I'm a little concerned about the timing of moving out of my current renting situation and buying a new place, fixing it up, and renting it out. 

I am looking at using flipping and BRRRR methods for my own personal REI.