Some lenders allow exceptions for transfers to LLCs owned by the borrower, but it’s worth confirming first.Explore transfer tax exemptions: Chicago doesn’t make this easy, but there may be exemptions or reductions for certain types of ownership transfers.

@MIchael McCUe   I get it, it feels like an incredible weight that you could easily lift with bankruptcy.

I've calculated the lump sum costs to be $9,500 for buy and sell combined and a monthly reduction in cashflow of $347 due to the new loan and taxes.

That in addition to my other arguments got me a 20+% reduction in assessed value!

But if those payments feel like dead weight, Dave Ramsey’s “debt-free” mindset could be worth revisiting.Here’s a quick story to illustrate.

At one point Elon and Vivek talked about a 75% reduction in staffing of the federal government. 

Generally speaking, Boston proper is an appreciation market (low cap rates) unless you have a solid value-add play.

I enjoy college football, video games, and lifting weights. 

For instance, in my private lending, I dont really give a numerical credit score much weight, but I absolutely look at the composition and history of the individual tradelines on a report if the borrower is a smaller outfit, such as a single member LLC or similar solopreneur-type operator.

Better to invest in your backyard so you can learn and use your commissions for price reductions.