A lease with the option to purchase at market rates makes sense for right of first refusal if they have money to deposit.

If your State law allows it, you can ask for 2 month security deposit if you think they may become high risk or you can simple move onto the next application.regarding the mortgage in question and monthly debt payments?

Everyone wants to move out as soon as possible.Thankfully, I have moved out last month, but you haven't returned my deposit yet.

I had my handyman do it for 15K and now rented at a higher rate....Another property in Florida, the tenant left such a mess in the house (gum in the carpet, drawing on the walls, etc), and the property management Company (I think their name is Watson) wanted to fully refund the tenant their security deposit! 

I would go with workshop option, but get a deposit and signed lease before you start the conversion on the garage to work shop.  

Too much risk and sets bad boundaries for tenants.Many use Venmo, Zelle or just have tenants deposit at their bank (local branch).There are also several free DIY PM softwares that have rent payment built in, but they charge the tenants a fee to do so (that's how the companies make money).

I know this isn't your problem but if you are able to move before your lease ends I will pay you $1,000, prorate your rent to the day you move and return the security deposit together with the extra thousand and prorated rent the day you give me the keys.

To sweeten the deal, add non-monetary incentives like free carpet cleaning, a waived pet deposit for an extra pet (if comfortable), or a dedicated parking space.

If they damage anything, I am afraid the security deposit is not enough to cover.

Your assignment agreement should specify the amount of EMD you require and the timeframe for it to be deposited.