I was thinking of a secure drop box but unsure.

Due to the low inventory it allows the conversation to be had to get a rent back for free (I have had clients do that just recently, only had a $1,500 security deposit for a $1.2M house), or renting back at the PITI for the new buyers. 

Whoever lends me money will want a security interest in the property.

The tenant had a $650 security deposit, which I had assumed would come back to me to cover some of the damages.

The days of forcing talent to move to California to secure capital are gone and with capital formation largely happening and being facilitated online you can expect for this to continue to accelerate.  

Fence, security system, dishwasher What was the outcome?

How am I going to secure this loan??

It sounds like the tenant will sign the lease even if I don't re-key but is asking for it "to feel more secure".

Holding period is key for the type of financing you secure. 

I have secured financing and I am ready to do my first deal.