They could make legal arguments about hardship and/or off-sets for non-compliance by landlord, but this would require posting rent or coming even with rent.

Make sure to get legal advice on what you can and can’t do for bill back and what kind of notice period is required in your state. 

If scaling quickly is your goal, DSCR loans are a great tool for the refi portion since there’s no 12 month seasoning requirement like conventional loans, and DTI isn’t a factor. 

Obviously each deal is unique and requires proper due diligence. 

So I’m trying to come up with a game plan  Conventional loans do require 25% down on an investment property.

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. 

My requirements?

There are variables involved, and there’s of course skill and effort required not just calls.

That is often a matter of opinion and will depend on the attitude of your municipality.Most municipalities do not require neighborhood approval, but will offer the public opportunities to provide input which will be considered.

@Nick AmYou also may want to consider other matters besides taxes, such as state law requirements for management companies and serving as a property manager, especially with a tiered structure.