One thing that has not been mentioned is depreciation. I'm no expert, so I'm not saying I have the answers. But I have questions.
What will either boat be worth in 10 years with no major upgrades?
What will either boat be worth with a new engine/rigging?
How long do you plan on keeping the boat? I know that's a hard question to answer but I think it should be taken into consideration.
'72 My C&C 30 may, or may not have depreciated over the 11+ years I have owned her. If it did, it's no more than 10%. I could unload it at a 20% depreciation in a heart beat. The funny thing is that it's still worth 50% of the sticker price