The purpose of my trip is actually two-fold - I will be spending 2 days purely for leisure doing some sightseeing and I will have 3 days with property visits and meetings.

Branding isn't my main focus.

I just completed the inspection yesterday and it seems the roof will need to be fixed(over 20 years, the boiler system is very old(there are 3 boilers), one of the 3 hot water heaters(HWH) is leaking and the 3 car garage (which is one of the main reasons the property is compelling as an investment purchase) is not structurally sound and may need to be demolished.

I just completed the inspection yesterday and it seems the roof will need to be fixed(over 20 years, the boiler system is very old(there are 3 boilers), one of the 3 hot water heaters(HWH) is leaking and the 3 car garage (which is one of the main reasons the property is compelling as an investment purchase) is not structurally sound and may need to be demolished.

One just need read the law for a very easy understandingThe preceding sentence shall not apply to any foreign taxes described in subsection (a)(3) or to any taxes described in paragraph (1) and (2) of subsection (a) which are paid or accrued in carrying on a trade or business or an activity described in section 212.And then the reference from the above law to IRS Code 212(1) It has been paid or incurred by the taxpayer during the taxable year (i) for the production or collection of income which, if and when realized, will be required to be included in income for Federal income tax purposes, or (ii) for the management, conservation, or maintenance of property held for the production of such income, or (iii) in connection with the determination, collection, or refund of any tax; and(2) It is an ordinary and necessary expense for any of the purposes stated in subparagraph (1) of this paragraph.And for even simplified version, just look at the IRS guidance on the subject...What Deductions Can I Take as an Owner of Rental Property?

Are you asking if you can deduct depreciation for the purpose of local taxes?

However, I learned that if I convert this one to rental house, the cost basis has to be the purchase price instead of the market price at this moment. which means if I convert the house this year and sell it in a few years, the 100k appreciation happened when I was using it as primary residence is taxable. 1031 is an option but what if I need the sales proceeds for other purpose?

BUT it seems a bit daunting to get started.The main concern I have is that the big appeal comes from the fact that there are fewer and fewer parks every year from those that are sold and converted to some other use. 

However, the mandatory (since the home is still mortgaged) insurances (windstorm / hurricane mainly) escrows adds literally another $2,000 to their monthly payment.

You must have a definite purpose of a given number with a set goal for a set time and write it down .