It's hard to classify a whole diverse set of situations on a 2-ended slider scale of good vs bad, lol, but the context is helpful.

For example, if you classify a $10,000 roof expense as a repair, you get to deduct $10,000 this year.

I am not renting to the person and let them know that it was because the felony was classified as violent.

Legendary investors like Warren Buffett would classify a non-cash flowing investment speculation, in general at least.

Instead, we turned to local classifieds on Facebook marketplace to pick and choose pieces of furniture/décor, drove to the sellers location all over the city, paid cash for a lot of these pieces (which made accounting more difficult), and even hand-built and stained a coffee table, console table, dining table, and two side tables. 

Any idea how that is classified?

The accountant classifies it as a draw on owner's equity and you report it on IRS Form 1040 Schedule C.

I believe AirBnB takes care of this where VRBO is just a classified ad site.We haven't seen much AirBnB activity in Utah, but places like SF are famously changing city ordinances.Most Utah cities have approved zoning for lodging like Bed & Breakfasts, but they haven't addressed week long accommodations.  

You can classify this sort of thing as "start up costs", but those I believe are not deducted all at once if I recall correctly.

To find acreage you can:Pick up a paper and scan the classifieds, orDrive around.Search online sites like ebay or craiglist (filter as you search)Even realtor.com can search land for you in almost any area.Picking up some brochures from a realty office works too.