@Bryce Allen to confirm your thoughts on the Milwaukee market, any deals my clients have bought in 2018 in SE WI, that was 6 units or larger, have been off market deals.Current landlords are being marketed to by other landlords so heavily, the sellers have multiple buyers lined up if they ever decide to sell.It's competitive out there. 

You could say that I've bought in heavily to the wealth-building power of real estate!

I've also considered doing a STR on a lake or river near me instead, which would probably put me outside of these heavily regulated municipalities, but I only found a couple of Airbnb's on the river I was considering.

As someone who heavily works in the Oakland market and helps many clients there on a regular basis I can provide direct insight on this. $80k sounds very suspect if its supposed be with permits. 

We keep a detailed list of what is done on what day and how long it takes.I'll paste in a portion of a move out accounting, you can see that we don't indicate who did the work, us or a third party:Itemized Repairs and Related Losses to get unit back to move in condition:$622.00 Replace carpet and pad (see comments) $24.00 Kilz primer to paint flooring to block pet odor from new carpet $10.00 Purchase and install missing end cap in fridge$300.00 Repaint unit: walls heavily stained $20.00 Replace door jamb in bedroom (materials) $6.00 Replace toilet seat (materials) $80.00 Labor to complete listed repairs and remove carpet Total Repair Cost: $1,062.00Necessary Cleaning to get unit back to move in condition, all at a rate of $18.00/hour: 3 hours to clean kitchen: empty fridge, clean fridge and stove, remove canned goods left, scrub counters and flooring2 hours to clean windows: remove dirt from sills, wash blinds1.2 hours to clean bathroom: scrub floor, remove hair from shower walls, clean sink and toilet4 hours to scrub living room and bedrooms: mop floor, clean walls, deodorize bedrooms, clean baseboards (very grimy)-4 hours for normal wear & tear/acceptable landlord cleaning for one year occupancyTotal Cleaning Cost: $117.00

So a piece of property in terms of capital or ordinary treatment, relies heavily on the items intended use in the taxpayer's hand.It can turn an otherwise capital gain into an ordinary one.

Use Facebook that way you can heavily pre screen and stop wasting your time and gas on losers .

Your ability to self manage is heavily dependent upon the time and patience you have available to do so.  

And there's and multi-point inspection list once the guests have checked out.Palm Springs is heavily regulated, but also has the potential for big returns.

That would depend heavily on your personal financial situation.