Sam, I bought a 25 foot Safari and absolutely love it, BUT, I sometimes wish I had a 27 footer when I am confined to the trailer for two stormy days. Two additional feet can make a big difference. HOWEVER, I can get my 25 footer in places where others can't. I once pulled into a campground late in the afternoon and found a beautiful space under a tree. I asked the neighbors if it was available and they replied "yep, youre probably the only one who can fit in there". As for the choice between Classic and Safari- if you can afford the Classic by all means get it. By the time I finish upgrading my Safari to what I consider 'Airstream Quality' I probably could have paid for the Classic.
I am sure you will enjoy whatever Airstream you choose- they are by far the best.
On The Road, USA