As a rehabber, I constantly have to juggle money while praying that my "Shark" HML does not delay or will at least give me some of my money upfront to start the rehab.

REI would be a side gig, at least for the mean time until I can no longer juggle both and the RE starts to surpass my salary.

Property management isn't rocket science but does have an artform that takes a while to understand and juggle all the hats.

Trying to juggle working full time in the ER it will not be conducive for me to write but I am interested to hear what systems you used.

All this while juggling the 60+ hrs/week W2 job and family.

If you think you will work less, or have less balls to juggle by being self employed, you may be mistaken.Your lifestyle may improve (or may degrade) depending on how you how much you like or dislike doing the self employed things you must do.You might make more (bonuses) working W2 at 70+ hours than you will investing (in some positions, for some employers), others exploit their workers terribly, and treat them bad.

I have had several agents who lack attention to detail and are trying to juggle too many clients and those relationships have not lasted very long. 

Thought would be to use FHA to get myself a duplex in IN and live there while commuting back and forth to WA a few times a month while renting the other side out helping me juggle my two houses and utilizing the FHA loan. 

It is a balance of juggling multiple items all at the same time.  

I juggled this exact situation less than a year ago, trying to figure out where and how to set my sights out of state.