So you have bad financial terms working against you along with finding properties, making deals, getting financing etc Secondly - for me it's time consuming.

I am constantly consuming content.

When we moved, we turned it into a rental, hoping this would be the start of our real estate journey—something we’d like to continue once my husband retires.Some key details:My husband is active duty and will retire in 3 years.We have one final move coming up this summer to Raleigh, NC.Our current debts are crippling us—the high interest makes it tough to stay afloat every month.The plan me and my husband are thinking bout:Sell the rental property.Use the proceeds to pay off all our debts, set aside emergency funds and a down payment for our next home.Free up $1,500/month from debt payments, and that also can stash in a high-yield savings account.Regain full VA loan entitlement, allowing us to purchase a multifamily home and use the house hacking strategy for up coming move.Avoid capital gains tax, since April marks five years of ownership, and the tenant’s lease ends in May.This wasn’t our original plan, and we hate the idea of using our equity to pay off debt.

Looking for Experts:Deferred Sales Trust: I'm seekin a real estate strategist and attorney familiar with Deferred Sales Trusts to help reinvest the proceeds from my business sale into real estate.Cost Segregation: Also, need recommendations for professionals in cost segregation studies, especially for cabins and industrial properties.I truly appreciate any wisdom, experiences, or resources y'all can share.

@Cameron Porter half off of a $30-40K price may not be enough to make a purchase work.We've seen clients quickly get upside down with Land Bank purchases:(So, proceed with caution and hire a great inspector and contractor to go thru the property before you agree to buy it.

You will need their advice on your state & local laws to properly proceed.

The lease agreements states"If Tenant and all Occupants do not vacate the Property by the Expiration Date orearlier termination of this Lease, Landlord may commence legal proceedings allowed by applicable law to remove andevict Tenant and any Occupant from the Property"Do I have to provide a 60 day notice to the tenant?

.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

Unless you make the theme of the house around that famous person, I dont think consumers will pay a market premium on ADR to stay. 

I am pretty sure you can not do a 1031 and use the proceeds to do anything to a primary residence.