This has been an interesting read.
A good mate of mine recently bought a midnight blue boxter "05 model, the car feels a little funny driving around with the roof down with two guys in it if you get what i mean.
He opted for the 18 inch wheels and the manual box, the car is a demon, it grips, it turns and it stops fantasticly, when i went for a ride in it he had only had the car for 4-5 days and he was steering it like he was born in the drivers seat,
The car seems (like most porkas) very easy to drive,
i doubt you would be putting your bum into an "05 model though with the price you had in mind so perhaps put it off for a while until you can afford a newer model, it's like anything new, wait until they have released a few models before you jump on the bandwagon, mainly because it gives the builder time to iron out any creases.
happy steering.