I am wondering if that would make it nearly impossible to move in a good renter and thus should deter me from buying this house?

Finding a 4 unit that you can use an FHA loan, in highly desirable neighborhoods in Chicago is almost impossible.  

I chose to put it in an LLC first and the refinance has been more challenging but not impossible.

However with the low inventory basically across the entire country right now, it is nearly impossible to do a traditional wholesale deal with on market properties being that the property almost always sells over asking price.

Getting money, almost impossible.

The 1031 scares me as it takes me an average of about 1 year and looking at hundreds of properties to find just one, so the short timeframe feels impossible to find several in other markets to use up all of the funds.  

Because once it starts it’s almost impossible to stop.

Learn how calculate cash flow It's not impossible and it has tons of benefits, I just always recommend for beginners to simply just do one of the two (rent or flip) master the formulas behind that, and then move to the next one and do a BRRRR.

.- Feels impossible to buy in the Bay Area again.

That said, flipping isn't impossible--it's very possible to find the right kind of deals.