If you are already juggling your job, home, and other responsibilities, the prospect of meeting with tenants and renegotiating leases can be daunting.

However, I have also realized all the challenges that come with this path and that also being in the Military could become a "juggling act, " so to speak.

I'd say you should try to either find a property that requires a little of work such as painting so that you can do it yourself or use a contractor, but if you are talking a full rehab, you won't be saving money or time trying to juggle all that you have going on. 

Juggling between full time job/school and a family complicates things but i am hoping perusing a career in real estate will give me some freedom.

Ideally find a likeminded peeror two who has a few more years of experience in REI, and who is also juggling a very demanding day job.

I think the main concept you bring to front is what works for us at this moment being knowing on the back end that it may or may not save is problem I'm juggling with. 

However you can only finance so many and it could be hard to juggle a large number of SFR as far as property management as opposed to multi family.

BLUF: I have a couple of properties with equity to juggle and I'm not sure of the approach to best set me up for my next REI.

I ended up quitting because my Amazon business was quickly taking off and I couldn't juggle loans, my rental portfolio and my Amazon store. 

Juggling people around just to save $500 vs hiring someone who could do it turn-key is not worth the headache.