welcome!
Jeff,
First, you've found a great resource for a lot of information relating to the sport. And after you find a sled, aside from here, there are several mfr. related forums like this specifically devoted to discussions about the sleds.
I joined SW a couple months ago, when i was in the
exact same situation. Rented, and ready to buy a sled. Craigslist is a good souce depending on location. CA may be challenging (i.e. SoCal), but the huge population should help the cause. Sacramento and other cities closer to the snow will probably offer more, but you'll have to drive for pickup. Lots on ebay, but factor in the 400 or so for shipping - and you don't get to check out / ride b4 you buy. Decent place to get market values of what's selling - even if you don't find something close enough.
Here's Kelly Blue Book's snowmobile value charts.
http://www.kbb.com/KBB/Snowmobiles/Default.aspx
You can usually land somewhere between dealer trade in and re-sale/retail values. Also, keep in mind that this isn't the greatest time of year to buy a sled (peak / early season), but there are good deals to be found. They'll be cheaper when the snow is melted.
After looking around for a month or so, I bought my 1st ride a few weeks ago from a guy I met in the swapmeet section. He was local (we're in Denver), but I also looked @ sleds in WY, UT, etc.
14k is a TON of miles. That sled was rode hard (not sure about put away wet). If possible, I'd suggest a compression test on the motor/cylinders if you're looking at a high mileage buy.
For reference, I bought a very nice 2003 ski doo summit 600 144" w/ 1800 miles for $2800. Many of the sleds here will have aftermarket upgrades (cans, pipes, lefty throtles, risers, etc.) If you can, I'd up your budget to about 3k and you can get a nice ride, w/ relatively low miles and probably a machine that was very well taken care of.
figure out what kind of riding you're going to do, then look for the right sled. (i.e. trails vs. powder vs. climbing, etc.) I started looking for a 2 up to take my 8 yr old son out and get him into it, but quickly learned that a trail sled would not let me play in the powder here in CO.
I'd also suggest staying in the 600-700cc range w/o a HUGE track if you're still learning. Others might disagree, but my 600 goes over 70mph and it takes a while to really understand how to ride (if that makes sense) - unless you want to just cruise down some trails.
feel free to PM me if you have any specific questions, understanding that I'm a relative noob to this - but I have learned a lot over the past 2 mos.
good luck!