Attempting to get in the middle of 2 sophisticated parties with a competitive middle man already in the market (commercial brokers) is tough.

Calls like:"Unit 1 had tons of people over every weekend for parties and clearly uses way more water than us.""

In my case, I have residential rentals in one LLC, commercial properties in another, self storage in a third, and my real estate company operates in a fourth.

Be mentally and emotionally prepared for the attitude - well, if you can afford a second (or third or fourth home) then you can afford all of this.

If you are looking to build quick capital and another full-time job, then flipping may be the answer...if you are looking for a slightly more passive approach and looking to build that long-term wealth, buy&hold'ing is maybe a better strategy.I've found introspecting on where I want to go long-term has helped clarify my short-term path...The beautiful part is Chicago offers all options at affordable prices general speaking compared to other metro areas.

In my case, I have residential rentals in one LLC, commercial properties in another, self storage in a third, and my real estate company operates in a fourth.

They now self perform all of their construction (along with offering 3rd party construction management services).

And I am not even a germophobe, when you travel in third-world countries you can't be, but I would not get into anyone's bath water if I don't have to, STR, hotel or gym.

I assume this is a 3rd party lender you are using and not the builders lender?

In my case, I have residential rentals in one LLC, commercial properties in another, self storage in a third, and my real estate company operates in a fourth.