alright where to begin with this.
1. your budget is not going to get you anything. every ski bum dreams of purchasing a sled for super cheap. the biggest issue with purchasing a cheap sled is they are pieces of cheap shit all the time. its going to break, no matter what, and it may happen when your 20km down a logging road or up a mountain. buying one because its cheap never works out in the end because you just dump more into it than its worth. one thing to remember is if it gets you out there you need it to get you back. its a machine, its not a toy and they are finicky so you want something reliable.
my advice, save up, 6000-8000 will get you a great working sled that will last you several seasons with no major issues other than blown belts, new carbides, and lots and lots of oil. and stay away from sleds older than 2007.
2. The whole "i mainly plan on using it to access trailheads for backcountry skiing areas that have semi-maintained snow roads, so not for deep pow sledding" never pans out. unless you have another buddy with a dogshit sled like yours with the same goal. guaranteed, you will be the only guy with the old beater sled, your buddies will have nicer ones, you'll all have the intention of access like you said, and then push too far and they will have to tow your sled out. It fucking sucks having a shit sled and watching your buddies roop around becasue trust me, once you get a face shot on a sled its going to be hard to go back to your skis.
again, having a dirty old beater sled in this case sure works, but you have to have to have to only keep it for those days. and it wont stay like that for long.
3. Sled brands are like trucks. Every dude has an opinion about why their Ford is better than this guys GM or this guys Dodge. In the end they are all the fucking same and each one has their own little subtle shit part about them. Sleds are the exact same. years ago, say 2000-2011, sleds were hit or miss. Those years saw a ton of innovations in the form of engines, size, track length, track width, hood shape, frame shape, every single thing changed in those years. so a 2006 ski doo may have been shit because the top ends always went, but an 07 was a pretty good call. anything from polaris up unitl 2012 was stay away terrain unless you are good at overhauling top ends and re boring cylinders. arctic cats were decent but not until 2007 when they started releasing the M series.
In your price range (please save some more) you will be looking at something in the early 2000 range. Those sleds are heavy, have short tracks, overheat, and are just not fun to ride. Most sleds in those years, its hard to say what was good and what wasnt because each brand changed so much from year to year.
Best thing to do it just google 2001 ski doo, 2002 ski doo, 2003 ski doo etc. Look at body styles and that gives you a good reference as to what sled will be better. if for example you look at a 2011 Polaris Dragon VS a 2012 RMK Pro, its a completely different sled. The dragons were just starting to figure a couple things out then they came out with the RMK chassis. When they did that, things get overlooked like the running boards being made too thin so they break, or the pistons developing piston slap. You never was a sled in its first generation on the market.
Go with a 2007 Ski Doo Summit, or a 2008-2010 Arctic Cat M8. Both are still fun sleds to ride , have decent power, aand can get you to the goods as long as you know how to ride them. Oh I totally forgot about they Yamaha Nytro. Its a 4 stroke sled, never overheats on trail, is good on gas, the engines will last upwards of 12,000km, and use a pindrop of oil. Thats the sled you should look into. they are heavy as fuck but will never let you down. Im sure you can get those for cheap becasue the only people that want them are ski bums, and maybe forestry guys.
Anything newer, its all good. Arctic Cat, Polaris, Ski Doo, and Yamaha are your 4 brands making sleds. all make amazing products and its now just becoming what colour and sticker option you like best they all do the same thing.
4. Features, I mean again, old sleds they are all kind of the same they handle like shit in pow but on trail are great. you want a narrower ski stance, a long track 155 or a 163 (they measure tracks in inches), the longer the track lugs the better (the part that digs into the snow). Its all pretty hard when looking at old sleds because they just werent designed for mountain riding.
Things to look for when buying a used sled are low km's, buying from an old man, look for ads where the sled is in a clean garage. Ask how the owner was getting it to a sled spot if its on a sled deck great, an enclosed trailer, even better. Less exposure to road gunk the better. Ask what type of oil hes been using whether its sled brand specific synthetic or if its the shit you can get from Lordco. Ask if hes ever had it serviced or how he store its for winter. Buying from a dad is always the best because if anyhting breaks, they take it to a shop, pay for whatever needs fixing, and keep sledding. A ski bum is going to go the cheapest route possible so you may even find duct tape on a fuel like or rivets on a bent tunnel.
Also, Ive found a lot of the times you can tell a lot about the way the sleds going to run just by looking at the guys truck or garage. if they are dumpy, dirty, pieces of shit, the sled may look nice when you pick it up in october, but it will have had a shitty mistreated life so watch out. and never buy from a friend. best case is your friend is a nice dude and cuts you a deal and he kept immaculate care of it but if anything breaks, your just gonna get pissed at him and hes gonna blame it on you so just avoid a buddy deal if at all possible.
5. Towing. a sled will handle it. but not for long. and you will break something and it will be expensive I guarantee it. Having two guys on a sled looks cool in the movies when Parker is shuttling up Chris Logan to the top of the jump spot but its only done in small little pushes to get your buddy up there. From past experiences, the least amount of fun you can possibly have on a sled is when you double up a logging road. It fucking sucks every single time. Even when I take my girlfriend out who is 100 pounds and can sit infront of me while I stand, it fucking sucks. its hard on your body and just beats the sled to piss. Youll blow shocks, your bend tunnels, youll overheat the engine but push it becasue your buddies on there and you dont wanna seem like a pussy stopping every 5 minutes to cool it off, its just sucks.
A couple times a year is no issues, but a sled used to only double up loggin roads, and towing is going to break. expecially a $1500 one. oh and not to mention sledding in ski boots is stupid hard, youll not be having a good time. Mountain sleds are designed for 1 dude and his gear. thats it. The guy above me mentioned those workhorse sleds you dont want those, its gonna be a hassle, and you can only pick them up if you live in fucking minnesota.
In closing, Save up, buy something more expensive than your truck, only double when your buddies sled breaks, and you're going to have a good winter.
Sorry for the rambling I dont know if any of that will help or make sense but do not hesitate to message me with any questions anytime. Im not the best authority but Ive been around it all and have owned the shitty sled, and the bran new one, and have friends with every sled out there. Hope that helps man and good luck!
