Portable or table-top is a matter of preference.
I'd recommend a scanner as "future proof" as you can get. That is, get one that can tune as much as is presently available. The reason is as soon as you get a scanner for that particular analog system someone else you like to monitor will switch to P25 digital or something. The Radio Shack Pro197 and 106 are about as modern as can be had and are competitively priced, especially when on sale, compared to anything else in the market.
You can certainly save some money and get an analog only trunking scanner for that agency in particular. There's nothing wrong with that. But be warned you would be buying a radio that is already obsolete.
Pro-2021, Pro-197, DX398, BC348, Flex-1500, Quansheng TG-UV2, Yaesu FTM-350AR, Yaesu FT-897D