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.

From a purchase and tax standpoint, I would operate the business expenses as usual in the name of the LLC as previously done.

There's generational wealth transfer and tax considerations as well to consider as these types of transactions can by synergistic if done properly.

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

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

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). 

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. 

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.

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.