Most folks I think would agree that learning the digital trunking side can be a bit tricky; it depends on the scanner you are using, and most importantly, to what agency or count(ies) you are listening.
There's something to be said for the PRO-96 and/or the PRO-2096; the V folder feature (that has pre loaded systems) is a great idea, tho I suspect the data is a little old by now and would need updating. That's generally not a problem; in fact, there are a couple of pages floating about - including one on the Capitol Hill Monitors website - that contains updated files for a popular program for these 2 scanners called Win96. I'm sure that when you move to Indiana, you would need to do something rather similar.
Speaking of the Hoosier state, it might be wise to post a few questions on the Indiana forum, and let others tell you what is going on there insofar as digital is concerned. A quick check of the databases on this site for your Safe-T system shows that it uses a mixed analog and digital format, so getting a handle on a digital scanner now would, at least at some point, be a wise decision.
In addition, there are 2 other Indiana scanning lists that look to be excellant sources of information;
Scan Indiana at QTH.net
SAFET Yahoo group
Yes, DC fire rebroadcasts its dispatches on VHF hi, Park Police is strictly conventional VHF hi, MSP is a little tough as they are on a VHF lo band system that a simple duckie simply won't hear well. Your neighbor to the north/north east (Prince George's county) uses a UHF conventional system (for the most part - they do have 2 small EDACS type systems.....), and many of those sites are easy pickings from much of Montgomery.
I should point out that the PRO digitals cannot be computer controlled in any way; it's simply not in the firmware to allow this. In addition, if you like to hear military air (and you've no doubt noticed by now that we have a LARGE and ACTIVE thread on the subject), neither scanner works in this range very well. In both cases, a Uniden is your only real choice.
I'll follow up in the next message with some Wikipedia links (which is supported on this site) that will point you to the various pages we have with information on all the digital scanners available. Those pages will help you as you do your research, as will jumping over on the Indiana scanning threads mentioned earlier 73s Mike