I ask because you can narrow down your audience depending on what the deal looks like.

That means doing some research, networking, drive by’s (or google street view if away from where you live), identifying what your strategy is and who your target audience is, and taking actionable steps towards your goals, whether that be making some phone calls, finding a partner, getting your finances in order to be lendable, etc.

Next time you are down in Chicago let's meet up or vice versa (2nd half falls on me Im back in Elgin frequently).

We used to frequent the beach/ boardwalk which is about 20 miles away, now we're hanging out by home and almost never drive that far unless we have to.

It depends on whether it was technically a lien auction under the new rules, or a tax certificate under the old rules, but people frequently call them tax liens. 

Unfortunately, I'm surrounded on both sides by rather unsavory folks who like to party a lot and frequently let drifters/squatters/rehabbers etc. live at these properties.

I get asked this pretty frequently and my typical response is along these lines.If you're looking for work (which I highly recommend if you plan to do RE for the rest of your life) you should consider getting a full or part time gig at a property management, title company, real estate brokerage (as an assistant or admin), mortgage broker, and/ or work part time for a local investor either finding deals or doing cold calls.  

The most frequent now is a buyer assumes the tenant on purchase, then immediately issues eviction notice, based on their desire to occupy.

With that being said, I think you should look into mid-term rentals so you'll be able to plan your next move with more ease and don't have to worry about all the common STR tenant problems in a place where you live frequently as well.

Maybe works if you plan to self manage, but if you are hiring a PM, turnover costs for this type of model would kill all your cash flow if the PM is charging a full month's rent for each turn.I would also imagine this is partially a result of municipalities cracking down on STR's more frequently.