Remote control and locable thermostates,  water leak detetors and main cut offs.   

I’m willing to front some money for less turnovers down the road.

The part I don't yet understand is that if I had a tenant paying my mortgage for me for years, and it ALSO gained equity, how I am so far off any ROI. 

Make sure the Realtor you are working with is an Investor specialized agent, not everyone is and they may not know how to be strategic and be a good negoiator.

Run off from neighbors roof is causing wood siding on my townhome to rot.

I'd saying following your experience and scaling off of your flips would make the most sense as you can use skills/knowledge you've already cultivated.

I really think this strategy can work for anyone and can really help launch you off into the direction you want to go with real estate wether that be cash out refinance, HELOC, another FHA, conventional, BRRRR, large multi family , single family, arbitrage , STR, MTR, LTR etc.. 

The electric has been off so the sump pump would not be functioning. 

Maybe one day I'll be glad I did but that would mean something really bad happened so hopefully ill be pissed off forever haha

There is a special approach to doing that and you have little competition when you focus on those.