At this point, is it worth it to get my insurance involved to help motivate the HOA to address the issue or will getting my insurance involved slow things down?

I have 8+ units that I would like to install plank flooring/vinyl of some sort when the units turn over tenants.

I know that the hctax website lets you look up a name or adress but won't let you browse the entire database.I am asking because I think it would be a good way to find motivated sellers I believe.

I recently joined pro and I found out that there is no filter to sort out multi-family in "find deals"...

I recommend you talk to the seller, find out what his motivation is, and then see if you can negotiate something that fits his needs and yours. 

There are very few banks out there that will allow a seller held second without you coming out of pocket or using some sort of collateral.  

Sometimes, money can motivate people to actually clean up their properties.  

He said he was in some sort of bind.   

I am also finding that there are all sorts of trash in the gutter in the street in front of the property.

Actually sounds kinda like some sort of fair housing violation 😬