Again it seems it's personal choice.
I do feel that you either have to be able to fix your own or be able to afford to pay someone else to if you can't.
If you lack the ability to do it yourself or lack the money
to pay someone else it's going to put a huge crimp on your plans.
Size and complexity play a crucial role in this case and can wreak havoc on your cruising plans.
I like the comfort of a larger cruising boat but know it has it's limits, both financial and practical. That's why I don't believe there is the perfect cruising boat, just the perfect boat for the individual situation and need. It is a good idea though to have a serious dose of reality when buying
one, you need to have a dream to sustain you through the endless work it takes to find and prep, maintain and upgrade a cruising boat, you just don't want to put yourself in an untenable situation if your aspirations outpace your abilities.
That's when people fall out of love with their dream, just be real about what you really need and can handle.
I didn't have the technical or sailing ability I have now when I started, it's been a long learning
curve, I could never have owned and maintained all the mechanical and electrical
(electronics) systems on my current
boat when I got into it, now that I have that knowledge it does make things much easier. It also has the added benefit of making my wife much more comfortable with the whole scheme, especially when it comes to safety
at sea, she has excellent sailing and boat skills but not the technical skills, her learning
curve is much faster since I'm able to explain and teach with "on the job" training. Nothing like getting your hands dirty and troubleshooting an issue to advance your technical knowledge.
In that vein, if your still at the beginning stages of your technical maintenance
skill set there's nothing like a simple boat, the maintenance
issues are usually simpler and easier to learn, the sense of satisfaction gained from troubleshooting it yourself will only increase your satisfaction with your choice.
If your abilities are more advanced, then what the heck, go big.
You just don't want to get into something so far over your head
that the experience becomes a negative one. I sure wouldn't want to make some of the mistakes
I made on smaller, simpler boats with my current
one, the cost would have been too high and much more dangerous.
A reasonable bit over your technical and boat handling skill set is always a good learning experience, way over your head
may not be as rewarding.