Communicate clearly about timelines and potential obstacles.5.

If not for you and you prefer the traditional route, I would explore potential "up and coming" markets such as Acworth, Cartersville, and Douglasville, where the price-to-rent ratio is a little more favorable, and growth is apparent.

There is tactics and strategy about how to open up maximum appraisal potential. 

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.  

.- Cities like Toronto will levy another tax (Vacant Home tax) equivalent to 1% of the current assessed value of the property if the property is not occupied (rented, owner-occupied, family occupied, all count as occupied)- Land Transfer Tax: while the Province of Ontario charges anywhere between 0.5 - 2% of Land Transfer Tax when your transaction closes, you should expect to pay this amount twice if the property is in the City of Toronto .

What are your thoughts on its potential to deliver financial freedom quickly compared to traditional real estate investments?

Hi Dave, welcome to the real estate worldCollin, Denton, and Grayson counties are great picks with growing demand and strong rental potential.

Big potential downside- both a selling and buying agent are involved here and I believe they're expecting their 3% each. 

The benefits of Kissimmee for a newbie is analyzing property potential is very easy - you will have a ton of carbon-copy comps to look at and the online estimators like Airdna can actually be pretty accurate. 

If the seller handles the repairs, it’s usually not an issue, but you want to verfiy what your lender requires.Cleveland Heights checks a lot of your boxes (hospitals, strong tenant pool, walkability, and appreciation potential).