The lot shows the existing building envelope next to the proposed renovated floor plan and square foot addition. 

SW also does a virtual color consult which we have done a couple of times when were trying to compliment existing colors so we didn't need to repaint the entire house or troublesome unique bathroom fixtures. 

But if the market for large STRs is thin, the basement might not add substantial value.Selling: Selling could free up cash for other investments with better returns, especially if you’re uncomfortable with the low ROI and management required for STR.It’s a tough call, but if STR potential is there, it might be worth a trial period to see actual cash flow before committing fully to the basement investment.

That's why welcome trolls exist.

If the tenants are in a month to month lease and the landlord prefers it then you don't have to do anything as the lease should renew on a monthly basis, but it really depends upon the existing lease. 

It does seem competitively priced for the area.If anyone has insights into how the existing HELOC might impact the mortgage assumption or tips for negotiating on a deal like this, I’d greatly appreciate it.

Not only to cover the existing issues but the expected issues that will crop up as the house ages.

Premium increases are rippling through the market; the state is also always going to be financially strapped/high tax due to union pension commitments from past generations and the high tax, high services nature of Chicago.I'd highly recommend getting on a plane and driving around before you buy anything there. 

If you find a deal you can always make an offer contingent on selling your existing properties.

Balancing job and investing stress requires prioritizing properties and strategies that align with risk tolerance and time commitment.