If I buy a Blackberry Pearl (still debating model), will I be able to retain my phone number and current monthly plan (few months still left in my 2 yr. agreement)
I have the White (with orange stripe) 64k Cingular SIM chip in my Razr (sucks!) as of now.
There's no reason you can't keep your old number, especially if you're staying with ATT/Cingular. But many numbers are portable now form one carrier to another.
As for your plan, you may be able to keep the voice plan you're currently on and then have to add a data plan to be able to email and surf the web.
As a side note. If you have a couple of months to go with your current phone you may want to wait. BB has a new device which should be released hopefully in the next couple of months. It may be worth the wait from what we are hearing.
There is nothing worse then signing a new 2 year contract for an older model and then seeing a brand new shiny BB with better features come out a month later. If your not completely addicted already, you will be and you will want the new one.