You do not want to give a squatter cash before they leave and also should not surrender the premise until you have cash. 

Because, once you start investing in syndications, you surrender control of the exit strategy and its timing, and you have to continuously find the next attractive syndication in the year your current one cashes out, and you can never touch the profits these investments generate.

How should have it been done, well, if you contracted to perform, and repeatedly failed that performance, you compromise your position, if not surrender it all together.

Do I need to get any signatures from the tenant confirming he is vacating/surrendering?

But I would like to go forth with a Holdover Eviction if they do not surrender possession by the termination date. 

But on the long run, it is far ahead of many others.You never want to surrender or sell your policy as you will incur taxes.

Some of the things a lender might take a look at are...Cash in bank accounts (checking/savings accounts)Stocks, bonds, and other securitiesRetirement fundsLife insurance cash surrender valueCash-out availability on lines of creditNot every lender who can provide a proof of funds will take all of the above items into account, so you'll need to ask them beforehand.With regards to obtaining the proof of funds, lenders who provide them will typically have you fill out a preliminary application, and then you can request one thereafter.Hope this helps,Michael

The tenant was responsible to surrender the property "in as good condition as received normal wear and tear accepted".  

Or you can have policies that will show the same cash value, but the surrender value will be much lower in the first few years, limiting your ability to borrow from it until the surrender value catch up.

You can probably get a replacement certificate issued and then surrender it for a tax deed.