I've been riding for a long time, have ridden many a sled like everyone I have my own personal preferences so I will try to give you some objective advice here.
First NEVER EVER ride alone. If you are looking for a 2 up with the intent of going out alone, don't! I don't care how new, fancy, well kept or bulletproof, or brand they all can and do break and not always in the parking lot! There are lots of places to explore on the trails and many go out into the middle of nowhere, not a place you want to run into trouble!! When you do ride with a group of people, carry a tow rope and know at least enough about your machine to be able to pull the belt off so you can tow the machine out if need be.
That said.. on to what to buy. Engines. You can go with a 4 stroke or 2 stroke, liquid cooled or fan cooled.
4 strokes are quieter and generally more fuel efficient. The down side is they are heavy so taking them into any ungroomed snow especially if it's deep is not a good idea.
2 strokes are snappy and have the power to weight ratio advantage but you really need to use a good quality oil in them and that can get expensive. Like any 2 stroke they do smoke a bit when cold and have a little more exhaust aroma when riding.
Fan cooled engines basically use ambient air under the hood in conjunction with a fan to blow cold air across the top end of the engine. The benefit here is that you don't have the complication of a cooling system, the down side is that the effectiveness of the cooling can be a problem and in some cases can result in engine failure. Also the fan does sap power from the engine. However they are not dependant on snow conditions for cooling. Fan cooled sleds are the least expensive. Fan cooled machines are limited on engine size topping out in the 550 CC range.
Liquid cooled machines are just that, they have antifreeze/coolant to keep the engine at operating temperature. Most sleds have liquid cooled engines. They run the coolant through heat exchangers mounted in the tunnel and the snow coming off the track hits the exchanger and cools similar to a radiator. Because there is no fan, no loss of horsepower is experienced and these machines are pretty darn quick. They are also arguably more reliable and if they begin to overheat you will get an idiot light to warn you and if you are oblivious to that the engine will shut down till it cools off.
Little note on engine size. While many seem to be infatuated with having the biggest and baddest powerplant out there, a 600 liquid is to me the best option, plenty of power, not to bad on gas consumption and not stupidly fast. As it is a 600 will easily break 100MPH. Fan cooled machines don't top out that fast, my old 550 fan could get up into the mid 70 MPH range.
As for brands of what to buy. No matter who you talk to everyone has their favorites... but DON"T BE FOOLED every brand has had their fair share of problems even the brand new ones. Certain brands have had good reliable machines too just need to find out which ones (year, make and powerplant) and focus on them. The past few years have seen a very extensive change in technology both in the powerplants (can thank the EPA regs for that) and suspension/chassis. Powerplants now are all pretty much computer controlled, have EFI and are fairly complicated. Older motors with carbs are far simpler but require a little more maintenance and can be a little finicky at times.
Sled chassis and suspensions have come a long way. In the mid 2000's there was a radical change in the way sled chassis were made creating a more rider forward, higher center of gravity type of ride. This was done to improve handling although I find them to be a little more tippy than a more conventional old school design. Like anything there are compromises so the best way to judge for yourself is to ride them - not just for 5 minutes but take them for a good ride on varying terrain to see what best fits you.
Finally 2 ups versus single seaters... long tracks versus short tracks. 2 ups are nice having the option to ride two on them. The down side to them is they are bigger machines, and with two people on them the handling suffers some. 2 ups have long tracks which are nice for traction. Single seaters typically are much better handling as you have less machine to maneuver. You can get them with either short or long tracks, but the days of short tracks seem to be fading away since having a longer track gives you far more traction.
There is a lot to consider when buying a machine, the best suggestion I would give you is to talk to folks that are really into it, if possible go riding with them so you can get a feel for what it's like and gives you a demo on whatever machine they happen to have. What you don't want to do is let a sales guy make that decision for you, the best thing you can do is get well educated before talking to any sales guy!
You asked about trailers. I have a covered trailer. By far the only way to go unless you want you machines to get a nice salt bath while being towed and sit in the weather if you have no covered parking. It makes sense to me as it's very nice to essentially tow a portable garage and protect your investment at the same time. Yes it's more expense and more stuff to maintain but well worth it IMHO.
Good luck as you think about all this stuff, a lot to think about and consider but at the end of the day if you do ample research you will begin to figure out what is best for you.
If you have any specific questions post 'em!
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