OTF - all great points so far but I think I can solve your delimna with one simple question.
You mentioned your "fiance". Here is the question:
Will your fiance be fishing/cruising with you any? If so:
1995 V21 steplift
If not:
1973 CC V20
Plus OTF, if it helps you to know, I was in a very similar situation. Not a cc, but I originally bought a 1973 V20 steplift which I was going to repower. Has the 20" transom. Well, I've got around $2200 in it without a motor and had I repowered it would have had $10,000 but still needed a washdown, kicker bracket, controls, oil tank - bunch of stuff that would have added up to $12,000. While looking at boats and motors I ran across a nice 1994 V-21 on this site. It basically had all of this stuff that I mentioned above (new) including new rub-rail, 9.9 Johnson kicker, brand new trailer w/ brakes.
I bought a brand new Yamaha 150hp and repowered it. I now have around $13,500 in it but after I sell the other motor I took off I should have around $11,000. So for $1000 more I've got a 21 year newer, foam flotation, cuddy door, nice welded stainless bow rail, new rub rail, hull painted below rubrail with awlgrip for a great no-wax shine, built-in fish box under passenger side seat, recirculating livewell and baitwell, self-bailing, cuddy cushions in great shape, new gauages, geez I could go on...
I love the looks of the "73 cc BUT, I think you should go with a newer V-21.
Check out my gallery for pics of my '73 and pics of my '94 V-21. BTW - I still have the '73 and waiting for a nice spring day to put it on the market ;D
...and yes, from one old phart to another, I am jealous you got to go visit the Grand Poobah and I didn't... 
;D :-*
