I will not comment as to the tax laws and underlying rules - that is a discussion you can have with your tax advisor who presumably you are paying to help you.What I will do is provide practical and business guidance on tracking time.Firstly, there are apps available that can assist with time tracking where you can specifically detail your time, who you met with, etc.

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

A common misconception is that real estate properties under $1M have a smaller tax basis and therefore do not benefit from a cost segregation study due to the associated fees.

The ultimate answer is no (and I'm not a tax accountant).

Because of the nature of a tax lien, it would be difficult to obtain financing from a commercial lender secured by the tax lien itself.  

My tax professional is stating that I would need an appraisal to show the lot/structure are valued at $400k if I try to claim $200k as a donation.

I am not a tax expert, but here are my thoughts. 

Then you can do a 1031 exchange or sell it at a lower tax rate. 

For tax purposes, rental income is generally recognized in the year you receive it, not when it is paid.

Then there’s this glorious tax season where you realize how many things you get to deduct that others can’t, while sheltering your income with depreciation, and earning tax free income with appreciation.