So if you're looking at this at a later time, likely not up to date anymore.

Since there's a chance I might move away in about 3-4 years, I want to make sure I can rent it out later and cover all my expenses with the rental income.Can anyone recommend areas in downtown Chicago that would fit my criteria and might appreciate a bit over time?

The two clear issues you have on your side are the dogs and, after next month's accounting, the late rent. 

If you switch later, that is another set of problems.When entering a transaction is easy, but trying to balance, analysis reports is a challenge - Now is the time you need to take an accounting course - learn debits and credits and more.Pick and choose wisely.

Four months later, I flipped the house and paid off the HELOC, and will probably use it again

So my plan is to form the LLC later and just take the risk of operating without an LLC and just have landlord insurance and umbrella insurance to start out.

We had a tenant who decided unilaterally to move out two weeks later than the contractual end date.

I wish more people would use their primary home as an investment property later - it's one of the best techniques out there.Now, to help with some things:1.

If you’re in a situation where you’re getting numerous showings, how do you keep those initial offers interested just in case the later offers don’t pan out.

So they are financially misaligned on long-term performance (and I think this is why there are so many people who have had bad turnkey experiences) And, as someone who has done lots of rehabs directly myself, I have seen hundreds of ways that turnkey operator could take shortcuts (to the detriment of the investor but beneficial to their bottom line) which investor could never detect (or not until years later when it's too late).