Should I have them pay right now or out of security deposit whenever they move out? 

On this forum search screening,  deposits, utilities.

If I were in your shoes and you wanted to keep them on MTM I would have them still sign a MTM lease and make the one resident pay a deposit, assuming you can sign new MTM leases in your area.I personally would still probably shift them to longer-term leases anyway, but it's not a bad idea to feel them out for a few months.

It can be a looooong process here compared to states like AZ, with your deposit being held for more than 6 months, so you have to understand the process.

It can be a huge pain to get started but you do get your rent direct deposit every month.

Ziprent will write the lease, execute it, then get the tenant in the unit and collect first month's rent and deposit.

Others will collect first, last, and a smaller deposit.

Most legal disputes are over security deposits and for small amounts.

I also let him know that I would need 3 months of bank statements showing deposits going into his account from the business.

Laminate countertops can hold up pretty well and if damaged, will need to come out of the security deposit - lower cost product, so a larger percent of it gets paid for if damaged.