How should I handle a landlord/roommate leaving my rent checks lying around after depositing it via Chase snap app?

Ask him to write “Deposited”/date/his initials and give your check back to you as the receipt.

If you want to avoid the confrontation and just have the money out of your account before chase verifies the check images, I’d just go with a cashier’s check or money order.

I don’t see why you feel the need to defend him. He may be a nice guy, but he’s still a total asshat for being so careless and unconcerned with your financial information.

You can like and respect people who aren’t very organized. I’m guessing that “landlord” isn’t this guy’s primary identity. If you like him and you’re satisfied with the living arrangements, all you have to do is put it into terms he’ll respect. As in: I need my cleared checks for my taxes.
Save him writing another receipt, you get your check back. win/win

I’d pay him in cash and get a receipt. Just watch and see how loosey goosey he is with cash.

This is the Chase app where you can deposit iPhone photos of checks, correct? Schedule a rent-paying time – let him photograph the check and then shred it yourself.

Or ask some deposit slips and just mail the checks to the bank or deposit them yourself.

Maybe you can arrange to direct deposit it to his account?

That’s a good one @Judi. That’s what we have our renters do, but if he has more than one renter, as weird as this guy sounds, he probably wouldn’t know who deposited the money.

I was going to say use electronic bill pay to get it directly into your landlord’s account, but if he’s not setup, the bank will just issue a paper check to him, so you’re back to square one. That got me thinking; I have a friend who paid rent by depositing it directly into his landlord’s account using a deposit slip at the ATM since his landlord lived out of state. If your landlord/roommate is willing to give you his account number, you can fill out a stack of deposit slips and deposit them directly into his account each month.