I am not a Cutwater owner, but I can assure you that your mission is what these boats are designed for. We had a C-Dory 25 and comfortably spent up to 6 months at a time on the boat. Every night. Sleeping. Showering. What it really comes down to, though, is what the people onboard can handle.
An example: When we were cruising on the Erie Canal one summer, we wound up on city docks at the same time as a couple on a 55' boat. I struck up a conversation with the guy, and he was fascinated by the trailering aspect of our boat. I invited him aboard, and he was quite taken with the functional liveability of our boat... and the fact that we could get to all the good cruising areas so fast, thanks to being able to trailer. He asked if he could show our boat to his wife. When she stepped into the cockpit, she barely poked her head in the cabin and said, "Oh, hell no!" and walked away. 😀
For comparison, their aft sundeck (with a full size patio table and 4 comfy chairs) had more square footage than our entire cabin. The boat can handle it... it is up to the people involved to determine if it can work for them.
We used to get asked about our boat frequently when cruising. My suggestion to people who had never spent time together on a small boat: spend an entire weekend together in your bathroom at home. Bring in a camp stove so you can cook and an air mattress so you can sleep. Maybe a couple camp chairs so you have a place to sit besides the porcelain throne. If you are still speaking on Monday morning, then you might be able to cruise on a small boat. 😉
