We purchased the home on 12/22/2022 for $20,000 and sold it for $39,000 on the same day.

I may make an offer on a property that's been sitting for over 80 days.

Seems really silly for the city to enforce as if I’m not still under the same roof. 4+ unit buildings don’t have this same requirement. 

The deals are very conservative and are mostly wealth preservation with modest cashflow (3-4%), but they've performed for me even while many syndications originated at the same time have been failing. 

This would give you an opportunity to rent to the same person(s) for a few years.

Same is happening in chicago and surrounding suburbs.

We purchased the home on 2/15/2023 for $40,000 and sold it for $60,000 on the same day.

Are you talking about your purchase of another property in this statement or did you accept a 2nd offer to sell on the same house and mistaken say seller instead of buyer???

I’ve recently been thinking about renting out my current primary home (built & moved in 2019: value $550K: have a mortgage loan of 2.65%) and buying a new primary home (built in 2020: value $700K: thinking 20% down +80% loan to purchase) in the same area.

Just get a firm exit strategy in place (and a backup) for financing before you take action - most cashout refi products have seasoning requirements these days.