If one of the units you will occupy is larger in GLA/bed/bath count its okay or if its closer to work or school.

Look for same bed/bath count, same property type, and less than 90 days old.

The outcome is going to be one of the largest homes in the neighborhood with stunning finishes and fingers crossed with parking!

Train a regression model using square footage, bathroom count, or more advanced features to predict the price of the sales. 3.

@Cliff ConnorRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

By putting 10% down I probably will be less than breaking even every month ((like an extra $800-900 per month at very low/conservative rent prices)  with the building fully tenanted (as is condition not counting value add with renovations). 

So high bedroom count, relatively low price.

I wouldn't worry at all anywhere within 2 miles of downtown. you are in the very south of south side area commission but still very strong market. once you cross 104 it's different. 

There are STRs there and Greenwood but not a ton of them.I do want to say that you never want to count on appreciation to make up for a poor performing STR.

You'll need to know if your site will gravity feed to sewer, need easements to cross other properties, or will need a pump station or grinder pumps for each home.