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.

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.

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. 

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.

I would be less out of pocket eating my tax bill without write offs and getting into something with 5% down

Even it makes $100 per month, if you have 100 of them, it is $10,000 per month.Reviews are just reviews, tax is just tax.

This will be very close approximation, with some assumptions, like insurance and property tax costs.

Purchase price was $102k and tax value is at $106k.

. - Looked at the property tax.