Since Realtors use similar marketing strategies to get in front of sellers (mailers, cold calling, door-knocking, SEO marketing, FB ads, etc) as do wholesalers, prospective wholesalers see the value in being licensed to give sellers multiple selling options. 

Gutters will help prevent more water from splashing up on the siding I am guessing.   

Left opening for louver doors so the HVAC and Hot water heater were accessible as well as sump pump. all three bathrooms tiled What was the outcome?

If there is a claim and it comes out that it does it meet their underwriting guidelines they may be able to deny coverage.even if they would cover a 3 family, the building coverage will be for a single family (1 kitchen, one furnace, one hot water heater, etc).  

It sure isn't happening via cold calling.

Just did a phase 2 recently with drilling and water/soil sampling it ran $6k.

My tenant was hanging shelf and screwed into a water pipe.

You could also attempt to look up their phone number and cold call if you're comfortable with such.

Won’t this cause water to get trapped and cause the wood to mold and rot inside the concrete?

It's like musical chairs and this will keep driving prices until the market finds an equillibirium between supply and demand, which all free markets will do over time, but since supply and demand are not that flexible it has to be price that will reduce demand until we are balanced.Milwaukee is also seeing a little bit of an increase in imigration due to climate change: smoke, fires, drought, hurricanes, floods, fresh water - in combination with remote work and low cost of housing compared to most of the country.