I like to keep things as simple as possible, but I was excited to dig into this one because knowledge is power, and the better we understand these things, the more we can use them to our advantage in real estate.So here’s what’s happening—your CPA is basically saying you’re already showing a loss on your taxes because of all the expenses that came with closing, insurance, HOA fees, etc.

@Chris LauerRecommend 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.

Possibly!

I am just getting started, but willing to learn as much as possible.

Maybe see about getting it turned into a section 8 and showing the tenant how to do that so you can get guaranteed rent from government if its a possibility?

It is possible to utilize low down payment loans and live in great neighborhoods in Chicago Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Because of that, my whole strategy is optimized to spend as little time as possible on REI at this point (all I do is buying and oversight, trying to stay out of the day-to-day as much as possible). 

Try to find any documentation possible.

@Daniel LangRecommend 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.

While it's still possible to use older comps if they’re in the same neighborhood, you’ll need to adjust for differences in condition, renovations, and updates.