This would be primarily due to your competitive advantage of living in Chicago and knowing the market.

Just think tax deductions 😂👍🏼

The current use of the property as a two-family dwelling significantly impacts its value and marketability, which is distinct from single-family homes.The initial appraisal comparing your property to single-family homes is likely an oversight, as multifamily properties are evaluated differently due to factors like rental income potential and investor interest.

Due to the high turnover and increased vacancy throughout the country I would raise the rent, put them on a month to month, and be thankful that you have a paying tenant.

LTR is stable, slow, and risk is low but potentially not as much cash (right away).Comes down to what goals you have and your risk threshhold - I have friends in CO springs who do STR and MTR, and works out great - but also have folks who LTR in that area and it pays for them self and it a great way to save money in places like taxes and build equity.  

No, banks do not allow a seller held second now a days due to risk and new guide line changes. 

AND, if you ever sell without a 1031 before you die you’ll probably end up paying higher taxes in the end.

There are other communities that would have better opportunities to cash flow.Although there is no guarantee of future income on any STR, I believe that 2025/2026 we will see a good increase in travel, mainly due to EPIC opening and the overall attitude of 'the people' coming off of the election.

So, cycles happen and we will likely have another down rate cycle in the next few years but it might just be due to another economic issue, so sometimes be careful what you wish for. 

But I am open to ideas.I see this environment as quite challenging to find a deal that will cash flow reasonably well in my area due to HCOL and interest rates (even as somebody with some resources).