Paying off some or all of your properties may not make you the most money but it reduces your risk.

This is better than 1031 exchange as you can invest just a part of your gain ( or all gain).

Fixing some or all of the issues boil down to a cost vs. time. 

Pull out as much dead equity as possible or all you will be doing is buying your cash flow at a very high cost. $140K of equity is worth about $1166/month.

I’d say do some or all of the following:1.

A reasonable buying price considers you may have to replace many or all of these things in the next few years. 

Yes, this can be done and it is called and AITD or All Inclusive Trust Deed. 

High down payment or all cash.

[Around here] Batt insulation needs to fill the stud bay cavity.

There are some insulation brands/types that can make insulation more dense (i.e R30C) but in general you need to have a certain thickness in your framinign cavity for you to get the proper thickness.