Most if not all of these properties require SIGNIFICANT cap ex rehabs and conventional financing won't touch them; you'd likely need to go the hard money route at 10-12%, 2 points, 12-18mon turn around.

But it also is a money pit if you don’t have the experience.  

Every day I mark how many calls to leads I made, how many people I contacted (and was it email, call, text) from my database/past clients....how many social media posts I answered or made, etc.I don't know if that's automating, but every week I can quickly see how much of each money generating thing I did.Do you use Google Calendar? 

I've done and been a part of many Chicago zoning changes...they take a very long time and a lot of upfront money...unless you are planning to add multiple units and do a full renovation, the ROI is probably not there.

So I get 4-6X rent for not much more money.

Avoiding errors and being educated on the laws can save time, money, and potential legal challenges.

If you have a chunk of money to get going I'd personally buy the biggest thing you can if you don't I think house hacking into a 4 plex is great. 

I have the money to buy now but I would rather do creative financing and use as little money as possible out of my own pocket. looking to start with BRRR method but maybe should start with a wholesale first to fund that?

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

I mean to me this is nothing money.