Also 4th quarter of last year Packwood and county officially did discuss potentially regulating STR's by either limiting numbers or adding a tax to cover increases in local services that are needed. 

So I would like to get these things hashed out well beforehand as something to present to potential clients and have procedures for my company.

Investing out of state in the KCMO area sounds like a smart move; it’s such an interesting market with plenty of potential.

I'm an RVA native, born and raised and have had experiences that could if shared with you could potentially be a big help to you. 

The cleanout is about 10-15 feet from the curb, but they had to snake 70 feet, suggesting a potential city sewer issue.The plumber mentioned that if I report this to the city, they will likely request a secondary cleanout closer to the curb, which I would have to install at my expense (a costly job).

It was in our list to potentially expand our portfolio, but we already have 3 properties close to the shoreline....perhaps one day.

Those are old enough to see some that need extreme updating and could potentially have value add component with a decent spread.

The potential problems mentioned by the responding posters in this thread are real and well thought out.  

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.  

•Business Cards & Branding: You can list both services, but if you want to avoid overwhelming potential clients, consider having two versions—one focused on PM and one on real estate sales, depending on who you’re targeting.Best Way to Generate Property Management Leads1.Target Landlords Where They Need You Most•Most landlords seek out PM services when they’re in trouble—tenants not paying, evictions, property damage, etc.