The huddle I'm facing right now is I stay in HCOL (San Francisco) where investing won't make much sense due to high property prices.

The median home price has more than doubled in that timeframe, but Milwaukee is a fairly linear market, so the neighborhoods have mostly remained the same, but median home price is a dynamic indicator and will always stay current, so you can benchmark neighborhoods against the median for the metro area.Note: in the MF space investors refer to a star rating system. 1 star to 5 stars.

And with cleaners going in after stay, it gets cleaned way more than with LTRs. 

Think 10-15 years down the road and you will stay out of some risky situations.  

Many projects go over budget due to unforeseen repairs or delays, and having a financial cushion is critical to staying on track.4.

Stay out of what the Jones are doing and do your own thing. 

My job is remote so I can move anywhere, and my sister and I have plans in the works for care for my mother so that won't be a factor staying local.

I would say run from Home365 and stay far away!

Wondering what everyone uses to keep track of financials/documentation and in general just stays organized with all of their investing. 

I would stay at your job.