re: First boat: Cal 2-27, Pearson 28 or Islander 28?
And to add to the conversation, don't jump into the "electric propulsion" idea right off the bat. Not to think for others, but I'd at least be willing to wager that after a year you'll find yourself browsing back through the "for sale" ads, as by then you'll start to know what it is you truly do "need" and "want". Today it's all just suposition. That electric propulsion is going to be a lot more costly than you're probably thinking, as it's been a real-life subject around here quite often. Search the forums and you'll get a feel for what I'm talking about. I can almost promise you it won't be cheaper to build the electric motor than it will be to repair the one installed, at least I'm relatively confident in that not knowing the true story on what's in there. You won't recoup the cost of electric propulsion as it's still an idea that hasn't gained a lot of traction. Batteries take up a lot more room and add a lot more weight than you think. Even though it's not always prudent to enter into a purchase thinking about resale, I do know that it's unwise to not consider it.
The word "dinghy" doesn't necessarily mean a 14' Snipe, btw. Lots of folks consider anything under 25' a dinghy and some even under 27-30'. I will say that the transition from a 22' keel boat to a 27' keel boat was a LOT bigger jump than I had anticipated. I went in assuming, "what's the difference, it's just 5 foot". Famous last words I'm sure said by many more folks than just me.
Having said all that, I will add the most important piece to this thread: pics or it did not happen. So, at this point, none of us have believed anything you've mentioned because we've not seen photographic evidence. Proof is in the pudding, you know. Good luck and keep us posted......I mean, if you ever decide to look at a boat (which means posting a picture of said boat). :-)