I currently live in the Bay Area, but I’ve decided to start investing in the Jackson County/MO area.

Congrats on achieving a comfortable financial situation.Condos are actually riskier than single family rentals. 

The main downside is being dependent on the HOA—issues like poor management, rising fees, or unexpected assessments can hurt your investment.

@Kris Lou Be careful with agents as 95%+ of them really only know how to handle owner-occupied transactions.We don't do biz in Indianapolis, so this is unbiased info we hope you find useful:Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

2021 hit and that is when I became financially free and was able to retire from teaching at 55 yrs old.

Not sure if this helps, but here's my failed investment. 

From my experience investing in mid-tier and luxury hotels much larger is you need about 70% to make ends meet, you start getting happy about the investment about 80% and around 85-90% you fell like you are a genius. 

My goal is to create generational wealth for my family and to eventually have the financial freedom to say "yes" to travel adventures as a family. 

It seems where you've chosen to move doesn't line up with your goal of reaching financial freedom?

This means both parties have certainty upfront.Market Dynamics: Just like with other financial instruments, market changes may benefit one party over the other over time.