K3TN here. I've brought various HTs with me bicycling over the years, didn't really end up using them that much. As others mentioned, you can buy cheap HTs now that have all-band capability and you can listen to lots of stuff, but since now bring a smartphone on all rides and tours, don't need it as much for that kind of stuff.

Depends on your route whether you will be within range of any repeaters - you can check Repeaterbook here. Harder to tell if there will be any activity, as there are a lot of barely used repeaters on the air these days. But, if your route goes near major cities you will usually find some one willing to chat.

As far as antennas, I never found trying to operate while riding very useful. I did the gutter mount clip on antenna on my rear rack, a few other antenna arrangements. But I never like wearing earphones, a speaker/mic was unhearable and Push to Talk was always a challenge. So, I only operated at night, occasionally at lunch stops.

Good luck on your test - it is a fantastic hobby.

73 John K3TN