I've been trailer sailing for decades and I love it. I have also owned a 27' fin keel yacht for more than a decade, berthed in a slip, at the same time.
If you can find mast up storage near a ramp or crane, that's a great way to save money. It adds maybe 10 minutes to the launch time, and saves multiple thousands of dollars a year in wet slip fees, bottom paint maintenance, and diver fees.
Bigger boats take slightly longer to raise the mast. With a good mast raising system, even I can raise any mast single handed. I'm an not-in-shape 66 year old woman.I am limited by strength to lift the mast at one end, and slide it into position to attach it at the mast step.
If you want to keep the boat in your driveway for $0/month and day sail frequently, I'd recommend a pocket-yacht with a tiny mast that doesn't require a mast raising system. Think swing keel or lifting keel so you can launch off the trailer any where. Under 20 feet with a light weight, spreaderless mast, for sure. I've seen 80 year old men put the mast up with just their bare hands. Think Potter 15, Montgomery 15, Compac Suncat, Potter 19, Compac Eclipse, Precision 16, etc. In a boat of that size, you are limited as to how far you can go, because these boats don't sail faster than 4-5 knots. They are for near shore cruising in reasonable weather.
You can keep a bigger trailerable too, for longer trips. Many trailer sailors have a small daysailor and a larger trailerable.
Now a days, I have a folding Corsair Farrier 24 1992. It weighs about 3500# with the trailer. It's as fast or faster than a 35-40 footer, easily does 13+ knots, so it covers a lot of cruising ground and it's a joy to sail. It's very, very small inside, and very big outside. It's a wet ride if you go faster than 9 or 10 knots and you're in lumpy water. I'd love a new F22 - it's more refined and gives a dryer ride. The mast is 35 (?) feet tall, and very stout and very heavy. It's the max weight I can handle by myself. It's easy for me and my husband. It's easy for a reasonably fit man. We have an almost idiot-proof mast raising system. It can be ramp launched or crane launched.
If you have a little more muscle strength than I do, you might consider a corsair or Farrier in the 27-28 range. They are bigger inside.
I still have a highly modified Potter 19 and have taken it all over the west coast and western states for up to 2 weeks per trip. (But since buying the F24, I don't use it). I can arrive at the parking lot and be in the water in in about 1.5 hours. I used a mast raising system The average 50-60 year old man can walk the mast up on a Potter 19 without the mast raising system and save 15 minutes. These boats aren't offshore capable, and should be used in coastal waters. They can comfortably handle Force 5 conditions in the hands of an experienced skipper.
Judy B