A few thoughts on the matter... I'd been looking for a 1998 and newer Grady White 228 Seafarer for just over a year before I finally found my boat back in Deale, MD from a dealership called Tri State Marine. I'd owned a boat before called a 21' Arima Sea Ranger that had a skip top on it. For the Puget Sound, it was a decent boat with lots of fishing room but it wasn't anything compared to a Grady White after going on the sea trial run and purchasing my Seafarer. The Grady is 100x the boat that the Arima was/is, a much more comfortable ride, not as wet of a ride either and just an all around better built boat. I sold my Arima for $27,500 and bought my Grady White for $26,500 so I actually saved some money and upgraded to a tremendously better boat. I live in Seattle and the same boat as mine just sold out here on the local Craigslist for $55k, although it did have a few more options than mine has, like radar, a kicker motor and newer electronics. I also don't think those things combined are worth more than $5k total, or so, and I'd value my boat to be in the high $40k's to low $50k's, but again I only paid $26.5k for the boat motor and trailer. Anyway, in terms of pricing... I bought my Arima in 2017 and after a couple months fishing on it I realized I wanted something much better, bigger and more comfortable. So I've been looking off and on at Grady White 228 Seafarer's for years and have yet to see one as new and nice as mine sell for under $25k. To make a long story short, I think you'll be very hard pressed to find one as new as the one you put an offer down on for under $25k, and sure as heck ain't going to find one for $20k... even in 2 years, in my opinion. These boats hold their value incredibly well, especially out on the west coast and the Pacific Northwest, and yours being a 2006 with an asking price of $40k without a trailer, hardtop, kicker motor, radar or anything else really just proves what people are willing to pay for them.
I think that if you waited another month or two - January or February - that you'll see the prices dip down maybe even a bit further, but come spring time, they're just going to jump right up again to where they were, at least that's my opinion. Other matters you mentioned above would be the hardtop... I'm 6'2" tall and my uncle is around 6'5" yet neither one of us have ever hit our head underneath on the hardtop when standing or fishing. I think the hardtop is great if you're like me and very fair skin with a light complexion and sunburn rather easily. I love that it will keep you out of the elements like the sun, rain, sometimes even snow if you fish year round, and I think the biggest thing is that it looks better than the bimini top as well as increases the value of the boat in regards to resale value. Most guys want the hardtop as opposed to a bimini top and you'll likely get a much broader range of potential buyers interested in a hardtop if/when you go to sell the boat, and it'll bring more money. The canvas curtains/isinglass also keep out the rain and other elements, as well as the hardtop giving you extra weight in the mid/front section of the boat for better weight distribution and oftentimes can help with better ride comfort. Lastly, in regards to the hardtop it'll give you a spot to put radar, should you want it, or should the potential next buyer want it, should you go and sell the boat. If you have a bimini top and want radar then you'll need a radar arch, which can be costly, and I think looks out of place compared to the standard hardtop. My uncle's previous boat had radar on it and yes, we only used it a handful of times or so, and most of those were for "practice" if it were to become foggy or to familiarize yourself with the equipment. That being said, there were probably 2 times out of the handful where the fog was incredibly thick and you couldn't see more than oh maybe 25' in front of you or so. And at that point, I was very much appreciative that we had radar as well as a brand new GPS/chartplotter as I would've gotten lost without it. Because of that, I'll likely be getting radar for my boat here before the summer, even though it doesn't really "need" it and although I'd likely rarely ever use it. That being said, it's worth the $1k - $1.5k investment, imo, and is only going to increase the value of the boat as well.
In regards to the engine... the lower unit issue is something that can't be seen from the outside of the motor. It's called a dry exhaust corrosion issue, and it effects the inside of the motor where you need to drop the lower unit, look up inside the motor and see if it's rusted out, pitted or so on. This can be done very quickly, within an hour or less if you have a surveyor/inspector or take it to a shop and have it inspected there. Most of the time, and I repeat ... most of the time, you can tell if there's an issue because the seller will be hesitant about having a surveyor/inspector look over the boat/motor, or they won't want to take it for a sea trial run or just avoid any questions about the motor altogether as they generally know of the issue. And is likely one of the reasons why they're selling the boat. Oftentimes you can also tell of the issue by starting up the motor, especially if you're actually in the water, and seeing if you get any overheating alarms, if it won't get up to WOT or full speed, if there's any smoking or so on. Any decent surveyor/inspector should know about the potential issue as it's very common and a very well known issue. Tri State is a Grady White dealership and they said that they scoped the motor on my boat, also combined with a great sea trial run, I bought the boat without a surveyor to inspect it. Which is the first time I'd done so as surveyors at the time were 2-3 weeks out and I couldn't wait that long being that it was an out of state purchase. So, I "rolled the dice" so to speak but when I got the boat back home I had the local GW dealership drop the lower unit to double check when I had the boat in for it's winterization and they said "it looked perfect."
Good luck with your purchase, hopefully it's what you want and there's a favorable survey/inspection, as well as the motor not having the dry exhaust corrosion issue. I guess from my standpoint, I don't know what your offer is but my boat is only 2 years older, a 2004, and also came with a hardtop, trailer, the nicer rear seat cushions and so forth but I only paid $26.5k for it. Yeah, you don't need a trailer because you already have one but that's something you could've potentially gotten with the boat, sold it separately and made some of your money back. I guess what I'm trying to say is that, based off what I paid for mine and what came with it compared to yours, I wouldn't be spending anywhere near that kind of money for it. And I honestly mean no offense. That being said, your boat does have a Yamaha 250 vs mine which is only a Yamaha 225, but I don't really care about top speed and mostly use my boat to troll for salmon. I think yours has a leg up on mine in that regard being that is has the bigger motor, but to pay what I'm only guessing is likely $10k more for a boat with a slightly bigger motor, 2 years newer, but doesn't come with a trailer, hardtop, kicker motor or anything else... makes me think there's a reason why it's been for sale for as long as it's been for sale for. Again, I'm not trying to be a jerk or anything, I've just paid very close attention to Grady White 228 Seafarers for years, and I think there are much better deals out there to be had. But, if you like the boat and it's what you want, for a price that you're comfortable paying, then by all means... it's your money, spend it how you want to spend it. Good Luck with the potential purchase!
