The house had brand new paint and every thing was functional and very clean at the time of rental.

Combined I have about 2 hours maybe 3 in the whole thing for the $277.

I have also sold many single-family residences but still own a combination of over 300 doors.

I don't like that dumpster either... but it's more of a cosmetic reason than a functional reason.

If so, my understanding is that the LLC would possibly need to have its own "Commercial" umbrella policy that is separate from my current own umbrella policy.My insurance agent suggested that given that I will only own one property, that for now, I should not bother with an LLC, and just have the Business Liability insurance tied to the home + my current personal umbrella policy.Other option would be LLC + LLC Business Liability Insurance + LLC Commercial Umbrella Policy + Personal Umbrella Policy (which I intend to keep regardless) --- but the costs add up - thus, is this an overkill - what combination of LLC & Insurance would be best to setup for someone like me with one property, and possibly another one in the near future?

The key for your 1031 is going to be to make sure that the value of the Vacation rental is at least as much as the combined sales of the two current rentals.Annual rental to vacation rental with limited personal use if perfectly fine.

These deferred taxes on capital gains and a potential tax-free profit in the future creates an incredible combination of financial incentives for beginner to advanced investors as well as large developers and commercial users.Opportunity Zones are similar in some ways to 1031 like kind exchanges (1031's allow investors to defer taxes on gains from the sale of a property by reinvesting the proceeds from the sale in another property within 180 days).

Yes there's def non confirming 3 fams in 2 fam areas but you might have a chance if this is preexisting function of the property. 

Just brainstorming here and asking for advice, has anyone ever had experience renting rooms in a 4 plex for a combined rent that is more than the market rent of an entire unit?

This will be a combination of fix/flip, lease option and buy/hold.