I know they have strict rules they follow..

I live in Carlsbad, and they have strict guidelines for STR properties.

While it's not strictly necessary to have a CPA before starting out, having one can be beneficial in ensuring you're setting up your finances and tax strategy correctly from the beginning.

Most likely, the Homeowners coverage would have a strict windstorm exclusion. 

I have good relations with the owner but they are extremely strict on this because if the deal gets out, they will be more overwhelmed with calls than they already are.I found a tenant who seems on the surface to be a good candidate.

This is doable however my time to find, procure, and renovate rentals is very restricted due to my life on active duty.When looking strictly at the numbers a mortgage provides a better CoCR and a better ROE, but stepping back and looking at more plain facts it seems like leaving the house paid off is the best bet, thoughts? 

@Hong Zhu most likely schedule E, although we routinely review returns that are incorrect.

Or, a charging order may be granted.If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

If you post the bond and the "dysfunctional" solar company who is very strict in its collection practices makes a claim against the bond the surety is going to make you immediately wire in $52k until the dispute regarding the lien is fully settled.

I would be curious to know how many fairly seasoned flippers routinely find 70% deals.