Can you afford to sail? First of all, I have to say that I love sailing, I don't know why. I get a huge kick out of cutting two poles in the woods and tying my poncho to them and sailing my canoe down a lake. And I have my camping gear in the canoe and camp out where I stop.
I enjoy any type of sailing, from a sailfish (like a surfboard with a sail) to a huge expensive sailboat, they are all great as long as they handle well. I hate a dog of a boat that can't track and broaches. So you can
adjust your sailing to your budget.
You can make sailing as cheap or expensive as you want. If you have money to burn, it's easier. If you want to go inexpensively, it might be less convenient, but then, I consider making money inconvenient. If you don't want to give up your home and live aboard, it's still possible to sail often.
I purchased a sailboat on a trailer less than ten years ago. My wife cried (literally). She said I'd never be able to fix it. I repaired it, and we sailed it for a few years. I sold it at a good profit. Without investing any more money I have gone from a centerboard 16 ft. dinghy to a 23' Hunter plus
a 24 ft. Seafarer. OK, I have five boats, but only three are obvious if you visited me.
By keeping my boats on trailers I have the luxury of having them close by. I can go anywhere my truck can go, and launch them myself. In today's market there are boats everywhere. I only look at ones that come with a trailer, the trailer seems to be free. Or the boat is. There are so many boats that the trailer is the deciding factor. It should be sound and have brakes. The trick is to buy boats that are basically sound but cosmetically awful. Take your time, cruise the Internet. Buy in the late fall. I could have huge boats for the same or no money, but I need to trailer them at this time in my life.
You should look into a mooring instead of a slip. It's cheaper, and your boat is always set up and on the water. You don't "need" to trailer a dinghy to get to the boat. We carry an inflatable canoe (Sea Eagle from Amazon, called a kayak but more like a canoe) which we can carry in the back of the car. We show up, inflate it, and paddle to the mooring. The car is cheaper to drive than the truck, which could carry a hard dinghy or canoe, it's a hundred miles round trip. If we have a lot of stuff, we can bring the boat to the dock and load up, but we usually just make a couple trips with the inflatable. Don't get a "turtle" shaped inflatable unless you have a motor. We tow the inflatable on a very
short tether, and when done just deflate it and stow it, washing and drying the next day at home. We anchor out, and cook on board. My wife brings art supplies, her camera, and a good book. I bring a guitar and tools and dive gear. She likes to hold the tiller occasionally, read books and do pastels. I decided to ignore pastel stains on the cleaned and repaired boat. Last time out she wanted to do the anchor. I forgot to tell her about mud and she got very upset about getting mud on the jib. Big deal!!
I spend more on beer than I do on sailing. I'd rather give up beer than sailing. If I sell a couple of my boats, I'd be $$ ahead of the game.
Yes, setting up the trailer sailer is inconvenient, but so is making more money and paying someone else. We go for at least overnight, so it's only set up, or take down. Arrive early enough to do the job. Do all you can yourself, all boat work is a ripoff. Get digital charts for free or cheap. With the trailer you can work on the boat at home. Heck, I slept on mine the last two nights just for fun. My back feels better than when I sleep in the bed!
I wouldn't be thrilled with a motor cruiser. I literally hate motoring, it's torture for me. Sailing is a joy. I'd rather watch paint dry than motor in a boat. I'd rather be poked in the eye. Heck, I'd rather make money than motor in a boat. Strangely, I think 95% of the sailboats we see are motoring, even in perfect sailing conditions. I like to sail onto and off our anchor or our mooring. Perhaps because when a child we never thought of a motor on a sailboat. But, you have to wait for wind and tide. Fine with me, I'm not out there to make money on a schedule. If I was I'd motor, but not enjoy it.