I heard that if you move the personal mortgages to an LLC they could get called and we would want to avoid that3.

To avoid non-competes and make twice as much, I wouldn't be getting a W2 job initially in Chicago and would rely on 1099 income.

When I approach them for financing on my next property, I want to avoid raising any red flags due to my relocation and the status of my Tennessee home via how I file taxes in 2024 (i.e STR instead of my primary as it was originally intended).  

Regulations & Compliance: What's the best way to research local STR laws and avoid potential regulatory issues?

The standard rule is $250k per person who legally owns/occupies for the 2/5 year requirement. 

@Ngozi IwunzeOne way to avoid capital gains is to turn the flip into a rental after the rehab and then do a 1031 exchange into a more expensive property. 

Are we required to pay FICA tax on the deferred income? 

The real prohibitive costs come from the legal, compliance, and reporting requirements of registering a security.

This will avoid a lot of confusion. 

.✔ Maintenance & Repairs – PMs coordinate repairs with vetted vendors, avoiding late-night emergencies.✔ Time & Stress Savings – If you don’t want to handle calls, disputes, or turnovers, a PM is worth it.2.