garymalmgren said..
Hi Silas and welcome aboard.
Re your question.
Basically, which one would be "better" to learn on for a single person
I hope you don't think that with the right boat and a few youtubes you can do better than crewing with someone who has already made most of the mistakes.
Traditionally seamen (seapersons nowadays) served a type of apprenticeship.
That is still the case today.
The process is
1. Find someone to crew regularly with.
2. Learn as much as you can about sailing. boat handling and that particular boat.
3. Do the same thing again with another skipper and boat.
4. Then with a bit of experience under your belt you can decide between a Holland or a Cole. (Without referring to the internet)
5. Buy a suitable boat and sail in all conditions with a crew., Rain, no wind, strong wind, Learn to sail with no engine
6. Then start venturing out alone.
Solo sailing is the most demanding for various reasons,
I am giving this advice to save you money , time and woes further down the track.
Don't give up on what you want to do, just do it properly
All the best
gary
+1
Although it is convenient to browse the boat ads and articles on line, the best information you'll get is from talking to folks about their boats (preferably, whilst underway). I got my current boat as a private deal by talking to people at the yacht club. It is smaller than what I was aiming at, well below the upper end of the budget I might have had to have negotiated with the Admiral, and it could not be a better fit for my needs, including single-handed sailing. My previous boat was a trailer-sailer, which was old, small and cramped, but taught me a heck of a lot about owning and sailing boats.
There are three reasons why every boat you'll see on the internet is fantastic buy ...
1 The current owner truly loves it, which means its not for sale
2 The current owner secretly hates it, but needs to sell it
3 Its a new boat and the producers have sponsored the article in a glossy magazine
I'm not saying that everything you read is untrue, but there are reasons why the authors would focus on the boat's good points.