I believe he's an Alderman for the Dells area and manages at least 2 STR properties in the area.

My CPA says STR "A" can only deduct expenses for STR property "A", and only up to income level.

You're saying county records have your property down as 2 bedrooms.

In 2020 I purchased a 1 bed & 1 bath condo and I have interest in pulling out the equity to use it to acquire another property to move into.

It seems like a great market for that despite the property taxes.

Normally I put the property under contract with a real rough estimate.

When you tell your friends you are a real estate investor, they want to hear you are investing in flips and cool multifamily properties.

Rehab 🛠️Once you purchase the property, the next step is to rehab or renovate it.

I'm scaling into a commercial property and starting a boutique hotel.

You can speak to the lenders you are talking with about their debt to income etc. if you are getting conventional loan they will take that into consideration, if you go with a DSCR loan they look more at the metrics and financials of the property.