Having a mortgage on that home might change some of the answers so just be prepared with how much the property is being rented for, what the taxes and insurance amounts are when you reach out. 

Low property tax/lower costs to maintain, etc.3).

self-manage or local company - depending on your personal situation - amount of time you have/strengths in self-management, financial situation, tax implicationsSkip the big management co's - like any big biz they have one priority in mind

I'm focused on the STR strategy as I would like to benefit from the tax advantages that it offers but understand it may not work out.

Some facts of the house:Location: Nassau County, NY, Town of HempsteadYear built:1929Purchase price: 290,000 in 2013Condition: AverageLot size sqft: 5000Livable sqft: 760I'm seeing several houses in my zip code that have been demolished and rebuilt into new houses with the maximum allowable livable square footage selling between $1.0M- 1.2M.Which is a better option taking into consideration, profit and capital gain tax (assuming my household income of 80K)1) Should I sell this house as is at $450K2) Demolish this house and rebuild it without taking out a loan.

The "corp-like" structure gets into the way so it can be financially/tax disadvantageous.Also, usually recommnded to not mix business lines within legal entities. 

Also unsure about how taxes would play out (see CPA). 

Considering the high property taxes unfriendly laws towards landlords , inventory, and prices here, I’m pondering out-of-state investments for potentially better cash flow.

Are they the same from a Tax perspective, Ordinary income versus long-term capital gain rates?

I have a property manager that handles payments/tenant screening so I don't need anything too fancy yet, but I liked the dashboard visuals to see where things were at, and to be able to have all of my transactions and my PMs in one place for tax time.