If your main concern is money, don't buy a sled. I bought one in 2006 and 5 years later after I sold it, I calculated the cost to average 150$ a day with maintenance and sled gas. That's without the truck diesel and sled deck.
Here are a few things to consider:
Plan on being the sole user of your sled. Towing/getting towed sucks. So does tandem for long hauls. If everyone got their own, you can get further/faster/easier into the backcountry.
Learn to sled, as others have mentioned. This might take you 5, 10 days of sledding. Maybe a whole season depending on your learning curve. I'm still not 100% comfortable because I haven't spent enough time learning, going sled access touring instead. That makes me quite nervous sometimes in tricky situations such as avalanched logging roads.
Enjoy the sledding. This follows the previous statement.
Once you like sledding, you won't mind the high costs associated to the sport.
As far as which sled to consider: the newer the better. A summit rev 600 144'' track will get you most places. For deeper snow, steeper hills, and more fun altogether, a summit rev-xp 800 154'' is the ticket (or equivalent). Most important, get a powder track. Mountain sleds are for mountains, touring sled are for trails.
Buying a used sled is trickier than buying a used car, especially if you don't do your own mechanics. These things get abused bad. Engine rebuilts after 3000kms are common if not before.
I hate fixing other people's mess so my next buy will be brand new, and I'll keep it in that condition.
This might be a little late but also helpful I hope!
Joel