The insurance problem grows as we keep having more disasters (hurricane, flood, fire, pipe leak claims in the billions).

There are things I know I will never look at doing myself: plumbing, electrical, roofing, installing hardwood flooring, bathroom remodel, and I'm sure many more! 

The investment purchases are through the roof and a lot of that stems from the great STR/VRBO options available.

The example you give and I have to believe with those facts the GPs are boxed into a corner IE they need to keep raising money or selling guru plans so they have cash flow since their LPS are leaking oil so badly. 

It has one STR penthouse (5 bdrm 4 bath with 3000 sf roof terrace),  plus 5 duplex units (Each duplex is two 3 bdrm 2 bath). 22 parking spaces.

Ask the wholesaler how old the roof, water tank, ac unit and furnace are. 

So as a % of total asset costs roofs, turnovers, etc... are a much higher % cost than on a more expensive higher rent roll property. 

On my end, I've never asked for one even when there was quite a bit, as I buy investment properties and expect I may have to replace roofs, drywall and other things that might be moldy or contributing to it. 

I would also target COA’s with newly replaced roofs, and negotiate to have the seller pay any outstanding special assessments at closing.

Maybe we are being forced into a colder world, where people just buy builder grade BS, and things are just treated as roofs over peoples heads, but feel is something human that cannot be taken away, and a good agent understands this and their buyers.