Let her go, get the place treated so it is 100% roach-free, and then find a new renter.At the same time, I would have an attorney draw up a letter hammering the HOA for not stopping the roach problem because it is costing you money to continue treating and you are losing rent income.

He hired a mold remediation company and looks like there is significant amount of mold and the cost estimate to remediate is coming to 12k. 

If you have to change a water heater, which now costs around $2000 in Colorado Springs, that is a large unexpected expense that the owner has to pay for.

Those numbers would be ok, but do you have money for the downpayment, closing costs, capital expenditures, 15k for reserves?

Normally, if the policy values the loss on Replacement Cost, they will initially pay the loss at the Depreciated value, once the damaged area is rebuilt, then they pay the additional amount (up to the limit on the policy).   

Is anyone familiar with the cost of getting such land buildable? 

I was concerned that the houses don't meet the 1% rule but with older houses, you're losing in more repair costs. 

You can negotiate to have the seller cover up to 6% of the purchase price in your closing costs. 

We have had a Strctural Engineer out to the property and while we don't need to conduct repairs within the next 5 years or so, we will need to address both of these things at some point and it will likely cost us about 100k.Any advice on selling or holding for the long term?

This change is significant for the financial feasibility of ADU construction in Chicago since water service costs can be more easily justified when collecting rents from two additional unit.Also proposes to allow larger units and to allow ADU construction in any zoning designation.