First, congratulations!
Second, study a bit more and get that General.
To try to answer your question, a lot depends on exactly what you mean. I am assuming 2M mostly here.
If you mean mobile to mobile, while actually mobile, you are just not going to get reliable communication over those distances.
In reality, that sort of distance is quite hard for mobile to mobile on any frequency. On HF because ground-wave power drops off fast, and mobile antennas are pathetically inefficient.
If you are talking about choosing a spot (in the car or from home) to talk to someone similarly situated, 50 miles shouldn't be too difficult.
100 is pushing it for regular comms. Especially FM. Now SSB is a different proposition, but few cheaper mobile rigs offer SSB.
The antenna is the key in any case.
Most books will push a 5/8 whip for mobile use.
They are better because even with a relatively poor groundplane the radiation angle is lower.
But, if there are hills around, sometimes a 1/4 with its high radiation angle works better, with the signal diffracting over the hilltops rather than just hitting the side of the hills.
So, static mobile from the highest bit of ground you can find, with a 5/8 whip should get you 50+ miles under most conditions.
Now, if you can arrange it with your friends, horizontal polarization works better for longer distances.
Look up designs for a mobile 'halo' antenna. They used to be common, but as repeaters took over, a 1/4 whip works for most people and vertical, short range comms (to a repeater) became dominant.
Better still, for static mobile would be some form of collapsable beam and a tripod arrangement to hold it up - manual rotation works just fine, no need to get complicated.
With this sort of setup, running (say) 50w, from a hill, you could well get good 100 mile contacts.
Mobile to mobile, running 10 to 50W, reliable contact -- you are probably looking at ~25miles max.
But - try it. Experiment. Prove me wrong :-)
K7UF / G8FVM