I did eventually find a carrier in the Excess/Surplus lines that would write the insurance. 

You should look to see how you can cut the fat and automate where you are able.

The double transfer of title between LLC and personal name looks excessive.

My goal is to own more rental properties, and was wondering whats the best strategy to achieve this, with regards to what to do with monthly excess money. 

Use them as guides in decision making not hard and fat rules.

If they rented sight unseen, there should have been an as-is clause in the lease because of that.It does seem excessive given the handyman found nothing at move out (and assuming he did a good job of the inspection). 

You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.

You and/or CPA should be able to provide the depreciable carryover and excess bases, if any.

You always want to make sure your bidding on 1st lien( usually the mortgage) because then "normally" any other liens are not your responsibility and fall off from your responsibility(they can make a claim on any excess proceeds from the auction sale).If your title search shows the 2nd lien being foreclosed on, well now your caught in the middle.

But the values listed  look excessive to me.