Sounds like it is best to either use the HELOC or obtain a conventional mortgage rather than using a HELOC and then a cash out refi.  

You can surely buy cheaper properties and obtain the same debt pay-down, but now you've got 5x the head-ache, so right asset class is more about efficiency when it comes to debt pay-down.Tax shielding is similar concept in that more expensive properties directionally give you more building basis to depreciate, which means less net income to tax.

This my goal to obtain over the next 5-10 years.

Now I question if I will be able to obtain fire insurance.  

Obtain the necessary insurance as well to guard against any hazards or damages that may arise throughout the renovation process.6.

It's important to understand the zoning/code requirements and obtain all necessary permitting if you intend on operating your real estate as STR anywhere in the country.

Quote from @Kody Smith: without getting too deep into my finances, what my strategy is...1. take loans to buy properties (leverage)2. fix/flip for day to day cash flow income3. use some of the fix/flip income to buy consistent cash flow through:- business acquisition, - commercial properties (MF and store fronts),I have no intention of doing ALL of the management myself, I will hire management as needed (medium term goal)my expected core role is money provider, evaluating the numbers, making decisions, and connecting with investors, wholesalers, lenders, contractors, and property owners.while I am just on step 2 of the journey, I am looking toward step 3 to stabilize, and not worry about if house prices drop mid project or not (or not worry as much) So to be fair this is more about obtaining and growing a real estate business not simply buying rentals for cashflow.

We didn't because we needed to provide POS in order to obtain our STR permit being that previous owner had a permit on the property already.

They obtain and manage capital, whether it’s private equity/debt, bank financing or personal capital.

This will increase the return above what can be obtained on a passive investment.The flipside of having the power to control everything is that it can be alot of work (and a full-time job if a person is putting in sweat equity).