@John Chapman Since your insurance payout ($300K) exceeds your adjusted basis ($50K), you’re facing a potential $250K taxable gain.

If all three units are on long-term leases that don't expire soon, you'll likely exclude many potential buyers. 

Here are five dangerous provisions to watch for in an Operating Agreement:Dangerous Provisions to Watch:Authority to incur debt without investor approvalPower to make loans to other entities/projectsAbility to cross-collateralize with other propertiesPermission to use investor capital for other venturesCommingling of funds across different projectsWhy These Are Potential Ponzi Indicators:• New investor funds could be used to pay existing investors• Project-to-project lending can mask poor performance• Cross-collateralization puts your investment at risk for others' failures• Commingling enables masking of financial problems• Lack of project segregation enables fraudulent schemesProtective Measures to Look For:Strict single-purpose entity requirementsProject-specific bank accountsDebt limitations and investor approval requirementsProhibited related-party lendingClear fund segregation requirementsProfessional Best Practice:Request bank statements showing separate accounts for each project.

In terms of other factors, I'm not sure there's a lot because I did have some people express interest in filling out an application before, and I actually got really close with one potential tenant, but it was because of the alcohol policy that he ultimately decided to back out.

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

However, if the loan is assumable, that could also be very attractive to a potential buyer and could end up driving what they pay you higher. 

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. 

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.  

These areas often have 3/2 SFHs in your range, with decent BRRRR potential.

Experienced investors typically value properties like yours by analyzing cap rates, cash-on-cash returns, and income growth potential.