I'm doing some research now to identify potential areas to keep an eye on and possibly connect with an investor-oriented local agent in each of the areas we're considering.  

My carrier, Mercury, opted not to renew because my buildings turned 60 in 2022 (policy cost = $11K).

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?

But, you can't determine quality by simply what they charge.....as there are plenty of terrible agents who also charge a lot.You'll need to determine what value they bring to you personally and do a cost benefit analysis of whether the cost is worth it to you or not.

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

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.

Partnering with experienced investors can provide valuable insights.5.Creative Financing:Explore creative financing options like seller financing or private lenders to secure better terms.6.Rent by the Bedroom:In high-demand areas, renting by the bedroom can boost your rental income significantly.7.Local Market Analysis:Stay updated on local market trends and network with other investors for insights and opportunities.Always analyze potential investments thoroughly and run detailed cash flow projections.

And while the borrower doesn’t have to come to closing with this money (it’s rolled into the loan) it’s still there – making an FHA loan have higher costs and higher APRs because of it.Are there any other differences between Fannie Mae and FHA?

If we rent our house out, the tenant would likely cover our entire mortgage, but our HOA costs are high (they were raised a lot recently).

I would review the property's current and potential NOI (after you complete repairs/renovations).