There are thousands of pages on consumer protection laws and regulations that depending how you go about doing a subject to could be against these laws and regulations. so like most things - is itillegal - it depends.  

Its at a ski resort so it seems like it would be time consuming.

After buying this house, I partnered with others to invest in a duplex in the Wichita area.At the moment, I’m living in Tennessee, and I’m weighing two options: either selling my house and using the proceeds to buy a duplex in Overland Park or Wichita with my partners, or keeping the house for another 3 years, transferring it to our LLC, and renting out the entire property to maximize its rental potential ( $1400-$1600 ) I currently owe $200k on the property with a 6.5% interest rate, and my monthly payment is between ($1,700-$1800).

Aside from that, once I was to get it under contract for assignment, just looking for any potential roadblocks or anything like that just in case while I proceed with the process.

This was very hard and time consuming, but I'm on the other side of the permitting process and ready to build.I am estimating the 6 cabins will be about 900k to build and will be worth 2x that when built.

I’m not an expert, but I don’t think you could live in the new property if you 1031 nor would you be able to access any of the proceeds for personal reasons.

here are some ways to get cash flow:-tax savings on other sources of income from your real estate shielding it-selling an underperforming property and doing something with the proceeds-raising the rent on a property that was breaking even-refinancing a property when rates fall and using the tax free incomeso again, you need to have a broader view than "property X made $37 after all expenses in March." hope this helps

For long-term strategies, a cash-out refinance is usually more advantageous, as it preserves ownership and offers fixed terms.To proceed, start with a professional appraisal to confirm the home’s value, compare refinance terms with traditional lenders, and carefully scrutinize shared-equity program terms to ensure they align with your financial goals.

Do I proceed with continuing to rent it out and sell later, or sell now?

The landlord can then proceed with the eviction process in court if the tenant does not remit payment.