So I just bought a 554 wall phone. (This is my first one, by the way; I just got a new cord wired in and got it working tonight!) ... So I called Verizon's customer service to verify this and to ask if it would also work for my voice mail feature. He said that this is standard in the industry for rotary phones because companies know people still use them. He said when I'm supposed to enter in my four digit pin for voice mail, just dial it and wait four seconds (to activate #) and it'll work. ...
Well......I tried that today and it didn't work. ...
I never trust what the person at customer service tell you. They're just call center workers, not technicians, and only go by what their Lead told them, another call center worker with a title. (I should know, I used to work in call centers).
Instead of trying to hassle with manipulating the dial to get # or *, consider another setup that you know will work. A Rotatone is one, or consider getting a PBX that converts the pulse to tone. (The PBX will come in handy as your collection grows, and it WILL GROW!) I use one of my rotary phones in conjunction with a PBX and TT phone.
Only problem with using a PBX is it still won't give you a # or * option, but I've found that the vast majority of the time, phone menus are rotary-friendly and only ask for numeric responses, in which case I can just dial it, or it gives another option, such as a voice response ("If you want [blank] say [blank], or stay on the line"). The only time I use the TT is when I want to access some of the features of my account, such as call blocking which I know is going to want # or *.
Another option if you have a cell phone is using an Xlink. It acts like a Bluetooth for your cell phone, but has a modular port to plug in your rotary phone and you can dial out with your rotary on you cell account. The cell phone acted like a Rotatone. If I reached a phone menu that insisted on a # or *, I used the virtual keypad on the cell phone.