Addressing Housing Demand -California’s housing shortage is well-documented, and SB 9 directly targets the problem by promoting small-scale, incremental density increases.

The problem is these bigger markets are almost impossible to cash flow and to make them cash flow; I would need to have very favorable seller financing terms or a lot more money.

I had no problem finding places on Oahu back in 2005 - 2008.

But at least you have a chance, and aren't exacerbating the problem as much.

It depends on where you want to live, income, personality, and other factors.You could buy a large home and rent out the individual rooms to cover expenses, but this comes with problems.

I would also be careful talking to property managers - they may have no problem telling about "other" buildings, but change of ownership in their own building is a threat to their livelihood.

Most are fine with that, but a few will have problems with it and claim there are legal issues, etc..

The problem I ran into was that most buyers that wanted to do it, couldn't bridge the equity gap and the sellers needed the equity to go buy the next one.   

A quick google search reveals that Minneapolis provides assistance for first time home buyers so there seems to be a problem with funds for first time home buyers in your locale too.

Here is a great episode to check out about doing these small but impactful gestures to enhance the experience at an airbnb.