My dad lives in the area where I want to buy and is a contractor, but maybe with the time my husband and I have personally, we would consider a smaller, more cosmetic repair on a house rather than jumping into our first big rehab.

Do they have a salesperson/advisor that you enjoy talking with?

Enjoy!

I would just check to see what is covered by the “tune-up” by your local contractors.

Can you demo the bathroom and/or kitchen and have maybe a bid from a contractor to remodel which (I would think) would truly make it unavailable? 

I have vetted and used contractors over the years, but the only thing holding me back is funding.Also, if anyone is currently investing or looking to invest on the south and southeast sides of Chicago, please feel free to connect.

If you build (via managing a general contractor), you should (ideally) know more about how the property was built than if you bought an existing home--you know what's behind the walls, and ideally you might avoid anything wrong with buying an existing home with issues you and your inspector didn't catch.I understand there's risk to building--it just seems right now that the risk is lower than buying an existing house--a house where you simply cannot know every detail without tearing it down to the studs and doing a complete remodel.

We hired a contractor to renovate our basement, and they just "finished" self-leveling the concrete floor and framing.

Broke down the doors and stole all of my mechanicals + material on-site (resulting in ~$30K worth of damage)I just had a contractor walkthrough and talk to neighbors and apparently there is now a homeless man who has been sleeping upstairs (he wasn't present, however bedding was present).

Enjoy low tax cashflow year over year5.