We decided to outsource major tasks such as septic installation, plumbing, heating, and carpentry, while handling smaller projects ourselves—a decision that proved beneficial.

I feel like there’s a balance between being decisive and being reckless, and I’d love to hear how you guys approach this.

@Tyler Lingle I found a couple prior to even posting this (CIREIA Club) but was curious about others before making a decision on which one(s) to focus my time. 

It can provide a very misleading valuation.Your appreciation numbers reflect just below 4% a year (I used 8 year hold) on both properties which is below national average for this period and below what neighborhoodscout depicts for Chicago 10 year average. https://www.neighborhoodscout.com/il/chicago/real-estateLooking at this from the outside, I am missing a lot of details such as your interest rate, is there a prop tax benefit for long holds (by the way look up prop 13 for CA at some point as it may play a role in your decision to purchase once you relocate to San Diego), the neighborhood, appreciation potential going forward, any emotional attachment, etc.  

It’s a tough decision, but after comparing Hospitable side by side with other PMSs, I can confidently say it offers more options for most users.

So far, it’s going really well, and I’m glad we made the shift.For me, the decision wasn’t about issues with self-managing but more about freeing up time and mental space to focus on the next steps in our investing journey.Curious to hear others’ experiences as well!

In absolutely no way would I ever depend on such a broad analysis to ultimately determine my decision.

That may help drive your decision.   

@Griffin Brenseke The decision to sell vs hold a property is full of those little decisions you describe that make such a difference in cash flow.

It's been the best decision we have made.