The 16 will be fine most of the time. As with any small boat (and I include the 22 and 25 in this) you need to be prudent about when and where you go, but the 16 will be a great boat most of the time.
As for marinas vs. trailering, I prefer a marina. In fact, we don't even have a trailer for our C-Dory. It stays at Twin Bridges Marina all year and is kept in the warehouse out of the elements. They fuel the boat and we just call when we are driving up and the boat is waiting for us at the dock. It is a great, clean, modern facility that I highly recommend. Cap Sante is also a nice facility, but if I were to wet slip I'd do it at Skyline which is closest to the islands. We typically run from Twin Bridges to our cabin on Decatur Island (dock is in Sylvan Cove). Dock to dock is normally right about an hour and the distance is about 16.5 nm. From Skyline to our dock is about 35 minutes. From Decatur Friday Harbor is less than an hour away, Roche Harbor is a little more than an hour away, Victoria is about an hour away... Everything is pretty close.
I've never spent much time in Anacortes but it seems like a neat community. I'm not sure what you are looking for exaclty but some of the farmland nearby is gorgeous and has impressive views of the North Cascades and Mt. Baker. Good luck on the search and know that you'll be near some great cruising areas for your 16!