Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

Just be mindful that you can't 1031 a personal residence but it might be eligible for capital gain exclusion from section 121.

A person files for and get's whatever from of welfare.

Account holders can't take any write-offs personally for investments made in the 401k.

Personally, I wouldn't offer SubTo or a Wrap, For reasons I've written about fairly extensively. https://www.biggerpockets.com/forums/70/topics/1227199-the-m...However, I would sell on "Lease Option" and that may work for you.

I asked when the other person will retire.  

Your ability to connect with them on a personal level matters more than your offer.Think about it:  • The “Used Car Salesman” is only focused on closing the deal as fast as possible.

It is also worth noting that property management is often closer to 30% of gross rent for a short-term rental due to the much more intensive hands-on management compared to a typical 10% for long-term and as such, I agree with recommendations above that medium term rentals may provide the best of both worlds if you are able to tailor proximity to a local need, e.g. hospitals and travel nurses.Again, happy to relay my personal experiences in the area if you're interested.Best of luck,Patrick

.• I purchased a small 1B/1Ba condominium in a high rise building in 2004 for personal use.• In 2010, I moved out and decided to put in in service as a rental unit.• I was able to keep it well occupied and leased throughout 2024.• I sold the condo unit in late 2024 for a nominal profit.That brings us to today. 

.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ 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.