This has been a culmination of several conversations with boat owners, want to be boat owners, previous boat owners, sailor/cruisers, motorboat owners, etc.
Some of the conversations to me were hysterical, some almost became antagonistic, some were productive and insightful.
It's amusing that boat owners have about as many polarized opinions about boats as they do politics.
But the question overall is: What do you want out of your boating experience? Think of that, and plan accordingly, because every decision will affect your bottom line in your cruising budget.
Here's my answer (and if you disagree, tell me to pound sand, I'm fine with that, but before you do, read the first line again).
Your boating experience is completely going to depend on your level of comfort, whether that comfort be knowledge, security (literal and financial), accommodations. The experience you have is what you want it to be. If you want to be in a slip every night, more power to you--just remember it will cost, and transient slips and run pretty high, especially where they are at a premium (like Key West).
In Annapolis, I had this lovely full time cruiser ask me why I would possibly even want an air conditioner/generator set up. To quote: "You will be in such beautiful areas, why would you want to lock yourself up below?" Huh? It's air conditioning ma'am, not lockdown in a Supermax prison, I can open the companionway doors and head out.
However, that being said, we are grateful we have the option. It keeps my spouse happy, and if it gets too hot, I can get cooled down. With a history of heat stroke and the inability to sweat, this creates a level of comfort/safety for me. If I'm overheating, miserable and sick, I won't be enjoying the beautiful areas either.
And no, we really haven't run the a/c that much. We have three separate units, and we have the ability to only run the area we want. At anchor, even in the tidal swing, we have 25 glorious hatches to provide us a breeze from whatever angle. So, having the option of a/c is a comfort. Does it add a maintenance element, yes, so you will have to add that into the grand scheme of things. The a/c gets run back in the slip, it helps de-humidify the boat, and due to the huge hurricane boat sheds, most of wind gets blocked.
Gadgets. We are in a technological society, we depend on our gadgets. I have already found out that taking the spouse off of his gadgets cold turkey gets him a bit antsy. Something he's not used to. That being said, we both plan to work remotely, so satellite internet is in our future. The technology is getting better and cheaper, so we will wait on that. And no, I'm absolutely not afraid of North Korea killing off my internet. My concern with the spouse is that he still needs to fully be ready for Plan B if our electrical system on the boat went out. He plans to start studying paper chart navigation more.
Again, in Annapolis we met some folks that said, why would you want THAT? You don't need THAT! Well, we don't need a boat either, it would be much easier to hop on a big old airplane to the Caribbean and rent a beach house. Quicker and I wouldn't have to worry that if a blow came up in the middle of the night, my house was going to run into the neighbors.
So, what this little dissertation boils down to is: Do what makes you happy. Hang the rest. Just realize that it will affect the amount of money you spend, the amount of maintenance (DYI or paid). If somebody tries to tell you that you don't need something, consider their input, but if it's something YOU want to make your COMFORT better, than do it.
I admire people who want and are willing to sacrifice a bit to live the lifestyle they want. It takes self-control and planning. Tim and I are going on the long term approach, we won't be doing any major cruising for at least 3-4 years. During that time, we'll probably add and dump stuff as we need. It'll be part of the process.
But whatever your approach may be, if you decide to take the leap, it'll be for nights like this:
You hit the nail on the head. There are as many ways to enjoy sailing as there are people sailing.
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