It is always difficult to accurately predict just how you will use a boat. That becomes obvious when you walk the docks in a marina. Just look at how many boats aren't used at all. Probably over 50% just bought the wrong boat.
Spend plenty of time deciding on what type of cover. If a full cover for storage protection, trailering makes installing really easy. Not so easy if the boat is in a marina. If you end up with a cover that doesn't have Tenara thread, just watch it closely. My thread failed after 15 years (garaged) and I caught it in time to simply re-sew the places where the thread was failing. I didn't bother with Tenara for the re-sew. Very little sewing skill required for this. Basically, all you need is access to a sewing machine and average motor skills. Just trace over where the thread is failing.
The design of a cover (if you are looking at a bimini while underway) is important. If you are looking at an Angler, I assume fishing is a priority. Generally, cockpit covers and fishing poles don't get along. The exception is a cantilevered cockpit cover that folds forward on to the cabin top. Best is one that has standing headroom. That extra 15 square feet of standing room makes the little 16 a different boat in the rain. With a fish on, it flips forward and doesn't interfere with fishing. Most shops have a "standard" design but are capable of fabricating something that really fits your needs.
I have the option of keeping my CD 16 in a marina where I have another boat. No thanks. The 16 takes up little space at home. I can easily work on little boat projects when at home. No marina fees (or break ins). Trailering the boat to the marina takes an extra 15 minutes to launch instead of just throwing off lines, but that extra time is made up for by how easy it is to load the boat with the day's/week's provisions when at home on the trailer. Easy peasy to launch, especially if the wife is there to help backing the trailer, etc. And of course keeping it on a trailer allows me to launch in far off places. Even if that doesn't fit your present plans, the time will come when you drive by a distant boat launch and start thinking.