This is a family property for which I will be paying 3/4 of the most recent assessment value.

What you use is what you have to pay back.Cash-Out Refinance Cash-out refinance this gives you cash from the equity you have built up in your home.

Getting a bit overwhelmed with all the required County Level and City Level business licenses, STR permits and Tax accounts (Business Tax, Franchise & Excise Tax, Sales & Use Tax) to register with the state.

I was told by a local experienced investor that insurance companies will always go cheap with paying out to contractors in the event a property needs to be rebuilt. 

He tells you to pay him $5,000 (or much more) to learn all the "secrets" that made him wealth, but then he doesn't tell you that his "secret" was to increase earnings, reduce expenses, save up and invest.

For example, using 70-80% leverage could preserve your cash for more deals while maintaining strong returns.A blended approach might work: pay cash for smaller deals to avoid delays and borrow on more significant properties to spread risk.

My humble advice to anyone attempting to do creative finance is:Creative finance is for experienced investors who have access to capital if anything goes wrong.Learn the lawsDon't use a contract "off the internet", laws vary by state and are also regulated on a federal levelLearn the financing techniques correctlyDon’t skip parts of the processDon’t ever do a “kitchen table” closingUse the proper deedAn attorney can help you with the legal work, but the rest you are on your ownYour guru will not bail you out“Investing” in someone else’s deal by providing a small 2nd loan so the “investor” can pay for “cash to the seller” and for “closing costs” so he can do the deal is a very bad planKnow what problems can ariseLearn the responses and solutions to problems before they are neededKnow everything there is to know about Title and what that meansKnow who a "protected class" individual isLearn the "back doors"Learn human natureUnderstand timelinesUnderstand regulation enforcement (some of these "mistakes" have a 10 year statue of limitations ( they can charge you 10 years AFTER you do the transaction) and carry hefty fines and possible imprisonmentThe court doesn't accept "I didn't know" for an answer"Know that the source of the lead plays a serious role in some states and federallyKnow how much of a "profit" pushes the boundaries to invite an investigationYou can be sued by the seller if you don’t do things correctlyYou are automatically at fault if an investigator or attorney or regulator gets involved.

Am I ok with this plan to ride up the appreciation, mortgage pay down and rising rents?

Do you typically pay someone to install? 

If it's in the restricted zone (within 31 miles of the coast or 62 miles from an international border, you have the choice between using a bank trust and paying the fees mentioned above or using a Mexican corporation and bearing the costs of establishing and maintaining  the corporation.