I am riding a Trek 2.3 with 50/34 and 11-25. I'm getting more comfortable at a higher cadence, (ave. 85) and feel like I am always close to cross chaining. Where I live there are a lot of smaller but sometimes steep rolling hills. When I get to a hill I have to shift into the smaller chain ring in front almost everytime, but when I get to the top I run out of gear fast and have to shift into the big ring again. Would it be better to be able to do most of my riding in the small chain ring in the front? What gearing change should I make if any?

You're not going to get any higher gearing on the front chainring unless you swap over to a standard crank, where you'll lose your low end for climbing. Plus small ring and smallest gear makes for a more severe cross chaining situation. I would consider changing to a different rear cassette (12-28 or similar) so you are less likely to have to use the small ring on the smaller rolling hills. You can use the 50-28 combo for short hills.

I lived in your area for a while (Fond du Lac) and the more I rode the less I needed my small ring. Same thing will happen for you.

Anyway, shifting isn't a bad thing. The gears are there for a reason - no need to commit to one chainring or the other.

The situation that you describe is normal. An experienced rider will make the change to the little ring earlier and avoid getting bogged down in the big ring. Likewise, on the downhill side, shift back to the big ring as soon as your cadence starts to get too high. If you ride the same route long enough, you'll know which climbs can be done in the big ring. If the hill is short enough, getting out of the saddle and pedaling standing in the big ring is another option that should get you to the top faster, but it's more tiring.

One downside to a compact crank is the need to shift one more cog after each chainring shift, compared to a standard 53/39. When shifiting to the big ring, expect to shift 2-3 cogs larger (and the opposite when shifting to the little ring). Making a chainring shift without any cog-shifts results in a much too large change in the gear ratio, except on some really sudden changes in slope.

I live by the st croix so we have similar roads I would think. I have the 34-50 as well. I have an 11-28 in the back. For our smaller rolling hills, I will try to keep in the big ring and usually try to power through them with the 23. If I need to go to the 25...I should've been using the small ring.

For the steeper hills I will carry as much speed into the bottom of the hill and switch to the small ring and get into a good cadence with something in the middle in the back. The more I ride, the more I use both rings....small ring strictly climbing.

If your cadence is high (90-100), you can probably mostly use the small ring.

Keep in mind that there is a lot of overlap between the gear sizes in the small and large ring.

If you are shifting to a higher gear, you typically have more time to perform the shift.

Thus, you should shift to the big ring before you run out of cogs.

Often, the cross-chaining gears are duplicated elsewhere (that means there isn't any strict need to cross chain).

Many people use your gearing set-up effectively. You should not need to change it.

You might want to run your set-up through a gear calculator. https://sheldonbrown.com/gears/