The boxes are cheap, and the doors delaminate without too much trouble, which leaves the thermofoil prone to chipping/cracking/breaking off.

Cleveland is a tough one to crack man.

I'd like to start small with 1-2 STR tiny house(s) or other less expensive "alternate housing" options (yurt, airstream, etc).

What you're probably referring to are what I call "pseudo" investment clubs which limit their  discussion to a relatively tiny # of deals that also happen to be ones where the club is taking a cut from the sponsor (usually via a referral fee from the sponsor or a portion of the promote).

Ask about financing and see what their rates are AFTER they give you price quotes.The parking lot is currently causing significant flooding, along with numerous cracks, potholes, and tripping hazards.

Apparently, James walked over to measure the noise level and discovered Steve’s door was cracked open.

I don't really have enough information from you to give you very specific advice, but I can say that if there is any room in the rent, it's probably only a couple of dollars PSF which isn't going to drastically change your overall monthly nut to crack.

AirBNB and VRBO both are cracking down on the listings.

Change the air filters, make sure sprinklers are set and watering, landscaping done, check on cracks and leaks, visually inspect roof, also checking for pets, and how many people living there. 

Do you want to invest in an international coffee business as a small owner with a tiny share and no investor rights whatsoever?