I should also mention we shut off the breaker (to the garage) after confirmation from two electricians and our contractor that we had a serious fire risk.   

She's not going to have any leg to stand on in court if you get that far unless there's some explicit language prohibiting the owner from assigning responsibilities to another legally authorized party, and I'm guessing there isn't if another PM company was maintaining the lease and provisions - and the fact that the tenant was voluntarily working with the other PM confirms the acceptance of an authorized agent even if it's not explicitly stated, the same way if you accept rent from a tenant after a lease expires you imply acceptance of the lease terms continuing (which is why you should always have a holdover provision). 

I 100% agree with the intent aspect and that is an important premise, but the fact is in this particular situation intent for it to be personal use has been confirmed (by way of a public post).

They/you can't choose the carrier - their software assigns it.Fortegra is one of the carriers (paper in insurance parlance) that their product is written on.That said, Fortegra is A- rated I believe by AM Best so that isn't the issue.I'm going to take a guess and say that your umbrella is written with PersonalUmbrella.com (Markel) and they require all underlying insurance to be A-rated but also with an admitted carrier. 

Since the property was built in 1975 also confirm it does not have aluminum wiring. 

Once I get a few stable long term rentals maybe consider looking into such properties and cover aspects I am able to confirm. 

On a more enterprise scale, I employ RevMax software as well as a fractional revenue manager who looks at the prices daily on a market level and a comp set level. 

Never signed up for his program, but you don't really need his software to do section 8.

If I have to manage the property by myself, I am curious which property management software (Hostaway, Guesty, Lodgify, PriceLabs, Hospitable) is better for sending check-in, checkout messages, and other automated messages.

The simple reason is that you cannot even tell debit cards from credit cards without a special software.