First recommendation is meeting with the postmaster to be sure he/she is familiar with bulk mailing. Ours is only because of a little bit of training on his side, and LOTS of experience working with us on our side (mostly exposure due to us). Find out how close the regional drop station is. It is cheaper the higher up the sorting line you go, for some reason . . . so actually most expensive dropping at local post office ??? Also, get the rough numbers on the addresses in each route so you can estimate costs. If you are totally PO Boxes, it may be just one route.
Get the USPS publication on Bulk Mailing. I do not know which one it is.
We do postcards and folded newsletters mostly. Cost is exactly the same is under 3.3 ounces, though. Newsletters just cost more to produce, or lots more work to handle ourselves (folding/stapling). Make sure your logo and name are prominent on anything you send out. You gotta make sure it is recognizable to you aren’t getting dumped in the trash with the other junk mail.
Our newsletter package includes some recent local news/goings on, some events coming up in near future, and announcements of stuff coming up at our shop. We try to be very personable and community centered with this along with our shop stuff. We have even gotten local businesses to buy an ad to help offset my costs. Not a money-maker, but a help.
We have not yet, but I strongly recommend some sort of offer/coupon/returnable something so you can track effectiveness of the mailer. We cannot agree on the need for this, so it hasn’t really been a priority in the mailers. It is really, really important to find out how many people are reading and how much money their orders generated. It was really obvious the first two times we did it with huge sales increases for a couple weeks after it dropped. No hard numbers, though.