Should I price each individual piece as a stand-alone investment and then combine them for a final offer price or are there either hidden challenges or advantages to a sale like this that would either make it harder or easier to manage?

In fact, I've heard numerous house hack stories of individuals doing exactly what you have mentioned.

A recent Bigger Pockets podcast had a guest that indicated he got a vacation home loan for a property in Joshua Tree.

Not that it was needed… multiple inspections since show normal settlement and nothing that indicates a sinkhole.I would like to sell the property for fair market value, however I understand that with the “sinkhole” history the house will sell cash only, 15-20% under market value, since owner/occupiers will have challenges getting insurance and financing.Any ideas how to remove this blemish?

What if one individual leaves and a new individual joins in their place (I've never had that happen)?

I've heard that Ankeny may have restrictions on the amount of new construction for large multi-family properties, but does that indicate an unfriendly atmosphere for small multi-family investors?

Joint venturing and partnering with successful individuals can be a powerful strategy.

When an individual property is distressed and hits the market, it's not going to have those instant 12 offers and bid wars flaring up over them that you will see with those purdy perfect white picket fence Hollywood dream homes in areas with optimal school districts for their kids, etc. 

I've read here that they aren't but reading the city's webpage seems to indicate that they may be allowed depending on what "zone" it's in, and some limit on number of STRs per development?? 

This break-down all of the structure/land requirements you need for each individual zoning.