Love the energy and focus you’re bringing to real estate.

For a few weeks, a tenant of mine in Chicago has been complaining about an intermittent sewer-like smell from the vents when the heat is running. 

None of the online tools know about the interior condition or upgrades.Yes, use Redfin, Realtor and Zillow, but look at the photos of the sold properties and grade them on a scale of 1 (needs major overhaul, including plumbing, heating, electrical, septic) to 10 (just rehabbed to a high standard and needs nothing done) and use that rating to adjust your comps.

All viable paths require work, time, energy, risk, focus, dedication, effort..... 

If the answer is no, selling isn’t quitting, it’s reallocating your time, energy, and capital into something that fits you better.You could make the light repairs, get it rent-ready, and stabilize it again, but if that idea feels more like a burden than a strategy, it may be the right time to move on and put your resources into a cleaner, higher-performing opportunity.

Right now, we have window units and electric baseboards for heat.

Additionally, the existing structure can be upgraded with modern amenities, energy-efficient systems, and improved curb appeal to command higher rents.Future development on the RM-1 lot allows for constructing additional units, potentially transforming this site into a multi-family or mixed-use development.

I need it to replace me by handling the tasks that rely solely on me but are very time consuming and energy draining. 

The amount of energy you’re going to exert is not worth the minimal upside of shaving a few months off the timeline before you buy your next property.  

Somewhere with low supply and high demand, population growth, a diverse and robust job market (even better if there are a lot of recession-proof jobs such as in government, education, etc as opposed to boom and bust jobs like energy and tech), high appreciation of both values and rent, desirability (somewhere people choose to live, not cheap locations where people live because it’s all they can afford but don’t really choose to live), and ideally within 20-30 minutes of where you live, but up to an hour away is acceptable if you’re just getting started, or farther if you know the location on a house by house level and have personal connections there.