Should my tenant pay my overdraft charges?

[Jolene Adam]

I have a great long term tenant since 2002, who has never been late paying. 

Last week he went out of town and forgot to make his payment. We texted and he said he would deposit his rent on an agreed upon day, the day of his return. But he forgot again, and I bounced two checks and was charged $75 in fees.

We have a verbal month-to-month lease and have never discussed late payment penalties because we have never had to.

It's my bad because I shouldn't have written checks assuming I had his funds. But he also didn't make the deposit on the day we (re-)negotiated.

If money weren't tight for me at the moment, I wouldn't worry about it. Should I ask for all or part of these fees?

[Steven Hamilton II]

Not his fault you don't have a reserve. You didn't check the balance or have the funds there at the time. It is also not his fault your budget is tight right now.  It should always be in writing. That is your fault and your mistake not his.  The only thing I would consider asking in this situation is for him to cover a late fee on your mortgage. But don't push it. Consider it reasonable especially as I'm sure you'd like to keep the tenant for the winter.