I have both and I use them for different situations. A tractor is much more versatile than a skid/trackloader but can't do heavier work quite as effiently. If most of yr work is diversified go with a tractor. So,what tractor/ I have a B-26 Kubota with a 4 in 1 bucket and a quick attach backhoe. for any landscaping job other than moving heavy material,this tractor will run circles around a skid. But you deff want a 4in 1 bucket. It will save you a lot of time and extra manpower(raking,etc.) as for skids,if you are tall,I yhave found that seeing out of a Bobcat is difficult. I have a Takeuchi 140(10,000# machine) and it's very strong,easy to see out of and dependable. I have run Bobcat t190,773,s250 and find them clunky and hard to see out of,the old operating system (hand/foot controls)is tiresome(my Tak has joysticks)and tracks are superior to tires. I bought all of my equipment new and got 0% financing. I bought new simply because of what you have found out already,the prices on equipment doesn't fall off very much. Also I get a new machine without any bad history,warranties issues or abuse. If you have work for any machine it can/will easily pay for it self.(figuring $75 to $90 per hr @ 400 hrs per year could gross $30k to $36k) also buying new most dealers are willing to sell implements/attachments with the unit you buy and include it in the financing. I think if I was in yr shoes(living in Mi-I live in Raleigh NC,we barely have winter)I would look at a tractor(I have a Kubota grand L 4240 w cab,loader). I would think the opportunity to work my equipment in the middle of winter and get $100,$150 per hr pushing snow would be a premium reason to look at the versatility of a tractor.