Hi David,You should generally look for properties that are 2+ years tax delinquent as these owners are obviously struggling with the tax payments and would be more likely to accept a way out of their situation.

How the IRS defines a principal residence: “If a taxpayer alternates between two properties, using each as a residence for successive periods of time, the property that the taxpayer uses a majority of the time during the year ordinarily will be considered the taxpayer’s principal residence.”

IRC Sec 280A(a).Self rentals in the tax world are usually thought of as rentals that a taxpayer owns directly, or through a controlled entity, rented to another operating entity that the taxpayer controls. 

It is not taxed at long-term capital gains rates.Individuals are cash basis taxpayers for the most part. 

When a taxpayer's residence qualifies as the principal place of business under IRC Sec. 280A(c)(1)(A), he can deduct all daily transportation costs incurred in going between his residence and other work locations in the same trade or business (Curphey; Rev.

As long as that LLC is a regarded separated tax paying entity you should be fine doing what you're suggesting.

The certificate was redeeemed by the original tax payer however he did not notify the CURRENT tax certificate holder and they allowed him to redeem due to the extra letter he sent me.

Taxpayers, more than ever, will be claiming the standard deduction in 2018.With that said - You would need to analyze what your Itemized deduction will be and then take the higher of the two.

To statisfy the same taxpayer technicality we opened a single member LLC that is disregarded for tax purposes.

There is a safe harbor for small tax payers where if your repairs and improvements for the entire year is  lessor than 10k or 2%of the basis of the building, you can expense the enter amount.