Don L,
Later in this post I will include a copy of a post by BandB from a similar thread. I think it is very informative and should provoke much thought on boat shopping especially when making a large change (eg. large upsize, sail to power, etc.)
From my perspective, it is very, very difficult to make a good (personal) boat choice without first defining (in some detail) how you are going to use the boat! EG, Guests: often and many or almost never. Dock to dock, or mostly at anchor. Get there fast, or go slow while enjoying the travel. On the boat for months at a time, or weekends away, ETC. ETC. ETC.
Then make lists based on achieving the goals identified in determining how you will use the boat:
must haves; nice to have; don't want.
When we made a similar change from sail to power, we wanted an aft cockpit, a pilothouse, 2 cabins, gas (propane) stove and heat, single engine, etc. Equally important, we didn't want twin engines, screwed down teak decks, exterior wood trim, flybridge, etc. There were many nice to haves as well. Other boaters will (and often should) have widely differing lists, because it is based on how they plan to use their boat, and differing preferences.
TAKE YOUR TIME! Chartering when you have identified a serious contender (if possible) is a good idea to help ensure you have covered most considerations.
Remember, it all points back to what YOU (and wife/partner) want out of the "new" boat, not what others want from THEIR boat!! Also remember that compromises will enter the picture. You will be hard pressed to find the "perfect" boat, but several may come close.
Good luck, and following is that post I promised from BandB:
"You will get a tremendous number of opinions tossed at you. It's like any information, you have to carefully sort through it all. Almost all the information and opinions are good, but they come from many perspectives and you need to determine ultimately which of those perspectives is akin to yours.
A few simple examples. Galley up or down? No right or wrong but many like it one way and wouldn't have it the other. So think of their reasons and then how you feel. Size? Some will push small and some large. But listen to their reasoning and determine what is applicable to you. Number of staterooms. Well, we all carry different numbers of people different times. Style from lake express to ocean passagemaker. Well, the selection of the boat is very much geared to where and how you'll use it. If you intend to stick primarily to the ICW your needs are quite different from the person who intends to go to Bermuda, explore the Caribbean, cross through the Panama Canal and go to Alaska then pick up Catalina on the way back. If your usage is mostly weekend and occasionally a week at a time then much different than someone living on a boat full time.
Now when people are fairly universally saying the same thing to you about a specific boat, give that more credence. But ultimately, it's your choice, not theirs. But go through the process. This brings me back to a business philosophy I had. I didn't question the choices, recommendations or decisions, I always asked about the process of getting there. If someone came to me with a proposal, I'd center on what they'd done, what they'd studied, what they'd found out to get them to that point. Ultimately I feel choices aren't good or bad based on the choice made but based on how you made it. If you go through the process correctly, then you'll generally be happy with the decision. If you short cut the process, skip steps, your odds of making a mistake are greatly increased.
So to me it's like any project I've ever been a part of:
Project: Selecting a boat
Phase 1-Define the requirements. What do you want this boat to do, where will you use it. This should be a detailed list of deliverables you want. And, yes, I strongly encourage putting it in writing and modifying it as you learn more.
Phase 2-Explore and evaluate options against your requirements. That's the key. We actually had a sheet against which we checked off whether a boat met, or didn't meet or partially met each requirement. The key is having defined requirements so you're not just saying "I like that" but you're saying it meets 90% of my requirements and all the essential ones. You can compare two side by side. And yes, "wow factor" or "feel good factor" can be a requirement. I just see it and like the thought of it. But that is only one of many. This phase will have to talking to a lot of people and looking at many boats, in fact probably hundreds on line.
Phase 3-Pick the best matches and delve deeper. In systems it's determining the one you want to pilot. Same here just a different definition of pilot. This is when you then make the offer dependent on sea trial and survey. To help you determine which one to make the offer on, test anyway you can. Charter. Ride in similar. Meet and talk to other owners who might even take you on a ride.
Phase 4-Piloting the choice-Sea Trial and Survey. Prove your choice is what you think it is. When all goes well, this step is very valuable. It reaffirms your choice. When it doesn't go well, it is even more valuable. It prevents you from making a bad choice.
My point is don't try to jump in and just say, I like this boat or that one. Don't start at "what do you think about boat abc?" Don't short cut the process. Take whatever time it requires. "