Re: why so long?
When I was looking at Islander 36's, I ended up choosing one with a steering pedestal over a tiller. Looking back, I wish I would have considered the tiller steered boat a bit more. Much more room in the cockpit with the tiller, easier to single hand, cleaner lines.
The pedestal has it's benefits as well I guess but on your Cal 27, I would think it would just take up too much space.
Also, as mentioned, $5k could be spent on a whole lot of other upgrades that would be more beneficial, imo.