Insurance costs can vary widely in an area, get your own estimates.All best in your REI!

I either sell them on a land contract or do a lease option because I get more money upfront, the money I get is non-refundable (unlike a security deposit), the occupant takes better care of the place, and if I get the property back, I get to repeat the process and make more money off the property than I would as a rental. 

How to mitigate the risk of them up and leaving is to collect larger security deposits or have them pay a couple months rent.

However, one partner is hands on, lives in the area, and will be doing all the ground work; to include securing the financing, finding the deal, and self managing the property and everything that comes with that.

second just have the family give you a loan like any other lender secured by the property. at an interest rate you negotiate.. refinance and payoff lump sum.. 

During that time I would secure a mortgage to pay off the first and second. 

In that case a locksmith would help. if it is any other device made to secure the door, then use a drill or elecrtric saw to cut it.

I tried, before the crash, to take 80% equity out to buy another unit but had zero luck at securing traditional funding through a bank.

Because of this, my property management is going to help with organizing the rehab, and gives me peace of mind being a boots on the ground and security in knowing I don't have some random contractor running off with my money. 

Would this be a Security issue?