Another one is when you start to feel a little weight off your shoulders because you don't depend entirely on your boss.

Granted there is a cost in hiring an agent, Having someone analyze each deal with localized knowledge is worth its weight in gold.

Or do a househack and use the $250k 2year capital gain reduction.  

Every market is different, but paying cash doesnt necessitate a huge reduction in price - it might, or it might just make the offer more competitive than other bids that require financing. 

This allows for deferral of capital gains taxes until December 31, 2026, with potential reductions in the taxable amount if held long-term.

10) How often have you authorized a price reduction or incentive?

Also I understand the funds aren't available for the improvements so that is another obstacle that has me leaning towards price reductions to move on as soon as possible.The exit of lower tier SFH's is something very few investors care to consider when making their investments but deserves far more consideration. 

You can likely see where a 5% reduction in your taxes isn't going to do much to reduce your bill. 

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.

Talk to your CPA to see if you would benefit.It is an easy to determine if you should get it done.Tax reduction from Cost Segregation Study > Cost of Cost Segregation study = get it doneTax reduction from cost segregation study < Cost of Cost Segregation Study = don't do it