Question about Craigslist: should I go ahead with it? (Details inside)

The warning about money orders on Craigslist probably has more to do with the person accepting the money order. They’re not very difficult to fake, so if you were selling on Craigslist it would not be difficult for someone to pay you with fake money orders unless you are very sharp at spotting the fake. (And how many money orders have you ever made or taken, that you would be able to tell a fake one from a real one?)

She wants the money order because – assuming it’s good, and obviously she trusts you not to fake her on this when you’re going to be her roommate! – it’s easy to cash (at places where they do have experience spotting fake and real money orders, and will pay off on the real one being “as good as cash”).

By all means pay her with the money order if that’s what she really wants, but at the same time make clear to her that for the sake of convenience and lower cost, you’ll want to pay by personal check from now on. She may want you to pay a day or two ahead of the due date, in that case, so that she can be sure to clear your check in time. That would seem fair to me.

EDIT: Since the money order, when you use it to pay, is “just like cash”, you should expect a receipt, of course. You shouldn’t require a receipt each month with a personal check, since the cancelled check is its own receipt.

Another way to pay instead of using a money order is with a cashier’s check from the bank. It comes out of your account, but the check itself comes directly from the bank, so it’s guaranteed, like a money order. The bank will have evidence of the check and you’ll get a receipt for getting the check. I much prefer to pay my rent with cashier’s checks.

See if she’ll take a cashier’s check. On her end, it gives the same guarantee as a money order, if not more.

Read the lease thoroughly before signing, and make sure it protects you. If it doesn’t, demand it be amended before you sign or hand over any money.

Some of the best roommates I have ever had I found on craigslist.

Don’t get a money order though, get a cashier check. This is effectively the same thing as a money order but you get it from your bank. They operate like Cash but the cool thing is (unlike cash or money orders) can you add a note to them that will show up in your bank account records (IE: “Deposit for 123 Icicle Lane North Pole”) etc.

The fact that she’s asking for this reflects well on her, because she’s following the standard practice. Landlords don’t accept personal checks for the first month’s rent and security deposit in NYC. You don’t need to find a “fair compromise between personal checks and money orders.” You’re already compromising by agreeing to be roommates. Don’t worry about her stealing the $1,000 from you. She would be incredibly foolish to do so, since you must know lots of identifying information about her. If she stole the money, you would report her to the police.