First of all, you don’t say what your experience is or what your budget is. That makes definite answers more difficult. From what little you have said, and the tone of your questions, I’ll make the best of it. Let me know what your total time is, in what airplanes, and what ratings you hold.
I don’t understand your comment on landing between snow banks having a factor on tricycle gear. Tail draggers are actually more short and rough strip friendly, but you must know what you are doing, be able to dance on the rudder pedals and have some taildragger time. I know, I know, how do you get experience without getting experience? For starters, fly em on good weather days into easy airports. Do it lots.
I’ll get this out of the way early: It is very common mistake to overestimate your abilities with an airplane. Get a lot of time in doing things that approach your limits, and take very small baby steps. Do not combine weak areas, like taking your new tail dragger that you have 25 hours in out on the snow packed runway. Tail draggers like to swap ends, and differential braking is harder on a snow packed runway. That’s the concern. The required skill is to never let the tail get even a smidge out of line. Know your crosswind limits, and know that they aren’t the same on snow. Based on the tone of your posts, don’t buy a tail dragger.
Do not consider landing on an unplowed, or plowed then drifted runway. Do not take off when there is more than an inch or two of snow, depending on field length and how wet the snow is. If it’s at all short, there should be no snow. I used to fly commercial, and our ops specs prohibited takeoff with more than an inch. Lots of potential drag there. Know what accelerate stop distances are, and keep that cushion when taking off in light snow.
Second general comment. Always, always, always leave yourself an out. That means having enough gas, enough good weather, enough altitude, enough of a ceiling, enough alternatives if something goes wrong.
While they are not directly related, if you are not comfortable night VFR, DO NOT go flying into the western mountains yet. Your skill level is not yet adequate. Gain more experience here in the east first.
Some planes have an STC available to install a baggage tube into the tailcone of the fuselage for skis, fishing poles, etc. You have to be very careful with how much weight you put there because the arm is so great. I know the V35 bonanza has this, and maybe a few others do too. There are a few baggage belly pods out there, the 206 and Cherokee 6 I believe have this available. Lots of drag, little concern on balance. Aircraft interiors are ridiculously expensive, so don’t go tearing up the upholstery stuffing burred edges, dirty skis in between the seats. Don’t forget this is an airplane, cargo should be tied down. Flying skis about the cockpit in turbulence is not a good combo.
For flying into eastern areas, forget mountain training. I don’t think that’s a factor. Especially in the winter. Think IFR. Icing. Cold starting. Terrain awareness and avoidance in IFR. The idiocy of marginal VFR in precip and cold under a lowering ceiling. The fact of the matter is between weather and icing, flights to ski areas are difficult in the winter. You need the bluebird weekend, or close to it. That can happen, and it’s fun. Just don’t expect to make it a regular thing.
I know New England well, and one of the problems is many of the ski area airports have lousy approaches. How are you at NDB approaches where procedure turns are critical to avoid hitting terrain? Or if the approach is decent, it’s a long schlep to the ski area. Are you going to leave a car up there? Not much for rental cars anywhere except Burlington, Manchester, Portland, Albany.
I skied Jay Peak once where friends picked me up in Newport, which is 40 minutes to Jay. Worked out ok, gorgeous clear March day, but the next day was cold and I couldn’t start. Had to do a jury rigged jump off a VW rabbit.
If you end up doing this, I’d plan on flying into Burlington with a nice long ILS runway, lots of support in the way of heated hangars and pre heats, and rent a car to Stowe, Smuggs, Sugarbush, etc. Get a few years experience doing that and build your instrument time. Then you will know the area and your abilities better. Maybe take some good weather trips to Morrisville, Rutland, Newport or Mt Snow if you have a friend with a car.
This is not for the faint of wallet.
It sounds like you are fairly low time. Meaning no instrument ticket and under 500 hours. If so, stay fixed gear, but consider more than 160 hp. Don’t go under 150hp. Forget about tri pacers, Cherokee 140’s, 150hp Cardinals, geared engines, or specialty aircraft that will be difficult to sell. Your first airplane is a learner, not a keeper. The Beech small singles (Musketeer, Sierra, Custom) are dogs, got my private in them, have no use for them. (Bonanza is fabulous, but I think too advanced just yet). High wing or low wing is either or. The 172/161 warrior is your bread and butter. I don't understand Yuki's comment on limited resale on 172's. They are the most marketable airplane in the world. If you have the budget, a Cherokee 180/Archer is good, as is the 182/235 Skylane/Dakota. Skyhawk XP never made sense, it was built to be a floatplane, land plane performance and cost isn’t as good as the Archer. The 206/Cherokee 6-300 are excellent. Both have the reputation that if it fits inside it will fly. Recognize that you will be burning 15gph doing 140kts, and you need to know about cylinder head temp management. If you crack an IO-520 cylinder, you will get an expensive lesson on pulling back the power too fast. The Lycomings are better on that, have higher TBO’s, but cost more to overhaul. Well operated it’s nearly a wash between the two. Turbo can be nice on performance at altitudes above 8,000 feet, a little overkill on an eastern fixed gear airplane, but scary on the wallet. Another 2GPH, higher heat loads on the engine, and there’s always the possibility of blowing the turbo. I don’t know why you’d want a constant speed prop on a 172. Useless. Not enough power to warrant it, and in that airplane you don’t want the weight or the expense.
When you do venture out west, know that performance goes down in a hurry. Stay light. Go into big airports with nice wide long runways first and get to know your way around. Taking off on a hot day is a real eye opener. Winds out there are a real concern too. Downdrafts can exceed your climb rate. Scary stuff. Take some training out there, you just can’t simulate conditions in the east well enough to impress you. I took off in a 152 I was ferrying once from Arapahoe County, just south of Denver one summer morning at 70 or 75 degrees. Just me and a few bags, full tanks, headed east, no obstacles. It took forever to get airborne, and forevermore to get a thousand feet. I remember the front range in a 182RG, only pulling 17 inches of manifold pressure and a sucky climb rate. Turbulence there can loosen your fillings. You need a serious airplane to get over the MEA’s and into a mountain strip.
You’ll find that you really need the IFR rating here in the northeast. It lets you get above a ceiling and fly direct instead of pushing marginal VFR underneath, it sharpens your basic flight skills, and it gets you home when the clouds move in. In coastal areas you have fog to add to the list. In the winter though, you rachet into the stratosphere expense wise for all weather capability. You need known icing, and that means at least a turbo Ce 210. If you scare yourself with a blown vacuum pump or an engine hiccup, you’ll be looking at Senecas, Aztecs and Barons. Those leave single engine budgets in the dust, require good engine out skills to be flown safely, and need more runway.
Another option is training to get your instrument in an easy retractable like an Arrow or Cutlass RG. You will have 40 or so hours with an instructor, and by then be well checked out on remembering to lower the gear. Don’t laugh, it happens way too often, and as a low timer your insurance rates will reflect that. Your insurance company will like the fact that your first 40-50 hours will be all dual. Then you get ~140kts on 10 GPH.
One of my personal favorites is the 182RG. 235hp Lycoming. 160 kts all day long on 13 gph. Good load carrying and good speed.
I am tired of reading about continued flight into marginal visibility and hitting terrain or spinning out of control. So don’t become a statistic. Get the IFR rating. You need to build the hours anyway.
I know a lot of pilots and airplane owners. Hardly anyone flies to ski. Those that do have houses up there, park a car at the airport, don’t carry skis, skis are already up there, and fly on the weekends that they can. They generally own more sophisticated airplanes.
I have flown nearly every piston airplane made by the big 3, have several thousand hours and an ATP, and have flown all over the country. Let me know if you have any more questions.