I assume the security deposit is one month.

Here's what I was thinking...Can I ask him for a deposit to hold now that will then be used as his security deposit? 

Try to get her out, use the deposit to turn the property around, and try to find a new renter quickly.One suggestion: I would only forgive the July rent if she works with you to market and show the property to new applicants.

Context:*For my business - I had initially setup a profit-first system w/ multiple bank accounts at my local credit union*For the properties under management -  I setup two trust accounts (rents and deposits) with Chase. 

Write yourself a check made out to 'cash' and deposit it for the funds needed.Also, you may want to check if you need to KEEP 150% of the funds needed in escrow with the town.

Imagine if there was damage when a tenant left exceeding the deposit.

Hey Beth, most of the people I've seen in the space pay by wire transfer or direct deposit.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

Should I discuss some bullet points and do a small contract between me and the buyer or is there a standard contract for such that we can agree up on terms prior to handing the deposit to the title company?

This allows you to ladder investments if you're saving up for a big deposit or if you just want the option every few months to extract principal or reinvest.