I think your biggest issue with any "work-arounds" is going to be your legal liability and holding the proper insurance in case something goes wrong, which I'm going to assume you'd need to be properly licensed in order to be properly covered by insurance.

(Ideally I'd like to hold the homes a long as possible)Would love some feedback from the BP community

Then maybe 1500/month holding costs. 

If these type of damages occur in the future, I would recommend holding the tenants deposit, or if there is a claim to be made through the insurance you sell them you could approach that avenue.

Talking with an adjuster, Companies were buying hailed properties, holding them for a year or two, switching Insurers, then making a claim, when another hail storm came through.f.

They asked how we got a hold of a site from a private listing.

I might have to hold off renting till next month to avoid the scraping of a tenant off the bottom of the barrel last minute.  

Up until then I was cheerleading the earlier thought experiments about supporting lean/regular/fat income with ~$1000 / month per paid off SFH, thinking “I could bang that out in 5 years”.

I am in the middle of finishing 2 flips there and have 2 long term Holds there as well. 

I wouldn't want someone to hold back, I prefer honesty and straight talk.