To name a few HVAC for unit 1 is 20 years old and could not fully inspect the heat, the pipe to the sewer has completely dropped and is not connected, in basement the window header, subflooring and joists are damaged from termite activity, and their needs to be some tuckpointing and masonry work done for the exterior brick. 

I wasn’t picking on the way you said it.Would it shock you that there are attorneys out there now who specialize in going after private lenders, claiming their intended business-purpose loans are really for a consumer purpose and subject to all legal penalties, damages, and consequences?

It can also capture damage to the property for which the tenant will be responsible so they don't claim it was in that condition when they moved in.

Also how do I make sure all secondary damage such as gutters, siding, windows etc are covered and accounted in insurance claim.

Not having the correct team and systems in place and totally damage your reputation as a property owner/manager, if your team (the maintenance company) does not have the same vision as you.Perhaps there is someone out there and if so . . .

On another occasion I had them inspect the property after purchase and they informed me that due to the condition of the roof they were raising my deductible on any roof damage to $5K instead of the $2.5K for the rest of the property until I installed a new roof.   

Does Builders Risk cover any damage caused by an occupant prior to getting them evicted?

Have a 1960s 30 unit single story motel where we are coming up on some end of life issues: the cast iron plumbing is disintegrating underneath bathrooms, radiators are starting to leak, electrical is in poor condition, and just today, discovered significant termite damage affecting multiple rooms.

Did it lead to more damage to the furniture/property and end up lowering your ROI?

You have to do lots of damage control in that buisness and be a strong negotiator.