Everybody has their favorite place to order radios. I've ordered from
Grove Enterprises and
AES in the past with good results. Scanner Master is a sponser of this site, so it's a good bet too. There are many others.
Most folks find that obtaining programming software for scanners now-adays is the most convenient way to program ever-more-complicated radios. Programming frequencies, tones, alpha-tags, talkgroups, etc. can be a daunting task just using the keypad. Most people like the
Butel software for Uniden models and
Starrsoft software for the PRO line. Remember that you'll have to purchase the appropriate cable for the PRO scanners separately.
Programming Motorola radios is much different than programming a scanner, so your friend may or may not do a very good job programming your scanner. It'll be up to you to make a list of what you want to listen to, and by the time you do that, programming the radio with the software won't be that much more difficult.
You mentioned the BC785D with digital card. Keep in mind that the BC785D will not be "upgradeable" to support rebanding when it occurs. Currently the only mobile scanner models that will support rebanding are the BC796D and PRO-2096 (both digital).
Also, I'd be pretty surprised if the agencies you mentioned "go digital" as quickly as they say. Typically that's not how it works, but there are, of course, exceptions.
Brian