Secondarily, if we can have a year wherein we can significantly decrease our tax liability thought REI, we would use that year to convert some of our tax deferred investments (403b, 457b) to in-plan Roth conversions and pay the taxes on those conversions - hoping that makes sense.We are open to STR, MTR, LTR - we just want to make a wise decision that lowers our tax liability. 

Currently, the rental income would not cover the mortgage payments, but I'm considering refinancing if interest rates decrease (possibly conventional to free up VA entitlement) as well as adding a fifth bedroom to increase rental income.My Plans: I intend to retain the NC property due to a stable tenant with a recently renewed year-long lease.

That would be important info to know.Keep in mind that a 3/1 may have a significant decreased market appeal as compared to a 3/2.

The market here is slowing down a bit, especially on the retail side where homes are selling for over 500k.On the investment side, we've noticed a significant price decrease in properties in Flood Zone AE due to skyrocketing insurance premiums.

As the broker of Investing N Florida, I frequently encounter clients who prefer to wait for interest rates to decrease before purchasing a home.

Plus, insurance premiums are expected to decrease, and there are cool opportunities in Tampa for ADUs and tiny homes.

My family outgrew the home and I wanted to pull the equity prior to house prices decreasing.

A certain percentage of tenants will pay late, a certain percentage will default, and a certain percentage will require eviction.The “problems” increase as the desirability of the property decreases.  

This historic district might not decrease as much but, it makes me a little uneasy that they are telling you that you can get 20% over the current comps you are finding.

However, I have a few concerns:Pros:Living condition: 1400 sqft → 1700 sqft with some boutique featuresThe rental market seems good in this area.Another property is added to my existing real estate portfolio, which currently includes two other properties.Cons:Interest rate: 7% - No guarantee of decreasing the rate, which means there might be no opportunity for refinancing in the future.The current home is too new to be rented out.People often say not to buy property in Chicago due to high taxes and low appreciation.There’s no necessity of moving since I have a decent primary home.Any professional advice would be helpful.