Being that you are in the IT profession, it should be no problem for you. Though I am a Technician Class Amateur Radio Operator, I had trouble initially with regard to grasping the new technology and procedures, namely because the technology is far different than anything I have ever used in the amateur spectrum. It took me a while to get the hang of what needed to be done, but after studying the operations manual and receiving a few pointers from several RR Forum members, I was finally able to put it all together. I didn't have to worry so much about programming my scanner as much as simply learning the new technology.
I downloaded the latest software update for the radio via the Sentinel software, and then transferred that information from my laptop to my scanner (Uniden BCD436HP) via the included cable. The software was free to download. Then, I created a Favorites List on the radio, which included only the system and the talkgroups within the system that I wanted to monitor. Then, I chose only the sites that I wanted to scan.
It's really been fun thus far. Just keep in mind that these new radios take scanning and programming to a whole new level. Everything you have ever learned previously about programming a scanner (analog) is pretty much useless. That being said, I really like the new radio since I've gotten used to it. For my personal preference, it was worth saving some money to learn what needed to be done. However, your preference may be to pay to have it programmed for you.
Regarding your question about whether to upgrade programming software components for DMR and ProVoice EDACS during the purchase, I chose not do do so, but to each his own. I had specifics in mind that are strictly related to what is currently going on in Shelby County, so the latter options were not on my wish list. If and when those become an issue for me, I will deal with it down the road. If you think you will have a need for those upgrades, a purchase on the front end could help you in the long run. There again, to each his own.
Hope this helps!