Our initial goal has been to buy a property every time the Army relocates me (roughly every two years) and rent it out afterward.

A third party company that integrates with our system.

I was able to turn my place into two units so no shared spaced helped a lot. 

As it relates to lease end dates I've seen two things work here. 1) You can stagger end dates as mentioned above or 2) you can optimize for summer - this works better for us in areas where you see students or families with school age children moving to align with the summmer months.Separately, this is a great argument against month-to-month leases.  

There are two reasons this is a bad idea.Investing with an SDIRA (assuming it is not a Roth) will often result in paying significantly more taxes. 

For the last two years we have been sitting on the sidelines.  

Half a lot and two bedrooms.

I do have two really good mentors / coaches I work with that would be able to provide more input but they do charge for their time.

Other than the two principals, an executive assistant and two managers, everyone one else associated with Tardus is either a”wealth coach” or a “client success coach”.

Personally, I bought a 3 bed single family home soon after starting my job and had two friends from college rent which covered my mortgage plus a little extra.