If you can get $1400 for the commercial without any out of pocket expenses and new long term lease with rent bumps, that would sound more appealingGood LuckGino

You can find more info on 1031 exchanges at this link: https://www.irs.gov/businesses/small-businesses-self-employed/like-kind-exchanges-under-irc-code-section-1031Regarding the change of ownership from joint to individual, there might be a couple of ways to handle that depending on your state laws and the terms of your divorce agreement.

.• Bulk Waste Limit: Residential bulk waste, construction/demolition, and green waste disposal are limited to a 5' x 8' truck bed load or small trailer per day.𝐂𝐞𝐧𝐭𝐞𝐫 𝐕𝐢𝐞𝐰 𝐑𝐨𝐚𝐝 𝐌𝐮𝐥𝐭𝐢𝐩𝐮𝐫𝐩𝐨𝐬𝐞 𝐂𝐨𝐧𝐯𝐞𝐧𝐢𝐞𝐧𝐜𝐞 𝐂𝐞𝐧𝐭𝐞𝐫 𝐭𝐨 𝐫𝐞𝐨𝐩𝐞𝐧 𝐨𝐧 𝟖/𝟐𝟔This newly renovated multipurpose convenience center will serve as the first multipurpose site to serve both Sevier County residents and short-term rental unit cleaning companies.

My investment property is in upstate NY and I live out of state and am managing myself (via my brother that lives in town), not a house hack, long term rental on both sides.

You have a different kind of short term rental, and you are there. 

I've created a daily schedule and habit tracker that fully aligns my daily habits and tasks with my longer term goals.

In short, the deal has < 1% rule for rent to asking price and 50% can't be spent as expenses.

Get familiar with FHA and Conventional loan terms. 

With the season in Sarasota County considered November - April, what is the best way to market the property as a Medium Term Rental (at least 30 days)? 

Haven't heard that term used for data collection/skip trace.