These are purely my opinions and hopefully others can build upon this.

I was not aware an llc offered tax benefits, thought it was purely for protection. 

So from a pure investment standpoint, it might have been a better option.On the upside, I hit some great timing on the following items:1)  Reduction of local taxes in San Jose to build the ADU. 

Any numbers provided would be purely anecdotal.

All the legal “theories” about why it was “illegal” and voided any enforcement of the note was just pure garbage......promoted by foreclosure defense attorneys, along with all kinds of other bogus “defenses” so they could collect large fees from homeowners fighting foreclosure.....all the while the attorneys knowing these defenses were bogus, knowing they would never win, but it gave them a way to sell their services to desperate homeowners.Here in FL it was an ever changing shift in new “marketing theories”........”show me the note” “invalid assignments”, “FL 5 year Statute of Limitations”, etc.Yes, there was a lot of sloppy work by banks and their foreclosure attorneys, and some improper short cuts....robot signing, etc.  

@Ryan Tremblay, for 4-plexes, Owner-Occupier-Buyers are likely to have one big advantage over pure Investors:- they can borrow at around HALF of your assumed 6.5% Interest Rate (as well as not requiring as much deposit)!

When we know the investor who is using the funds are purely for rental purposes; these options are available. 

Conventional loans need 20-30% down, and then would allow a property to be pure rental with no owner occupied requirement, and less restrictions for the property.

And to provide some context, no, this is not how I evaluate deals, this question is purely for discovery what others in the Chicago market are seeing.

So you need to find a property where the price is justified by the rents, which means learning how to analyze a multifamily property as an operating business (which it is).There may still be properties out there where the high rents justify the high prices, and the property can still cash flow - usually because you can get a low interest rate mortgage that keeps the mortgage payment just low enough that you can eek out a profit.But you'll need to learn how to do that analysis, to determine which prices are still acceptable given the rents, and which are so high that you're setting yourself up for a potential negative cash flow situation.As far as it being owner occupied / living in one of the units, you're not counting the fact that by living in one of the units, you're also not paying rent somewhere else, so you get a personal use benefit which does save you money.That can be hard to calculate though, so what I usually recommend to people is that they analyze a multifamily that they're going to live in, as if they're not going to live in it, and instead rent out the owner unit at market rent.That makes it much easier to analyze as a pure investment, and compare it to other properties, see if it's cash flow positive or negative, etc.And as an added bonus, someday you may want to move out - either to a single family home or a different multifamily house hack.