Collect interest and payments over time while maintaining an interest in the property.1031 Exchange: Sell a property and reinvest the proceeds into a similar property to defer capital gains taxes.

What I would recommend, is looking into TAX LIENS AND DEEDS.

Law: Illinois has a law that requires (I believe) the insurance company to give a 'General and Special Taxes & Demolition Expenses' Form (Important info for this issue) to the city when claims/damages are over a certain dollar value.

These include fix & flip and DSCR rental program that don't require tax returns of W-2 jobs, but rather uses your credit and property income to qualify.

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).

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.

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

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.

After this year's tax bill I need to do something different to reduce my tax liability.