Skids and compact tractors hold their value well, even when old. I have a JD 3203 with loader and 500 hrs and I can sell it for 4-5K less than I paid brand new in 2006. That said, I would either buy lightly used (basically you save the initial depreciation) or new. I have had several tractors and I strongly encourage you to look hard at kubota if you buy a tractor over a skid. I currently own a john deere and I know many here may disagree but I feel the current Deeres aren't built as well as the older ones. John deere 4300, 4400, 4500, etc. (older models) tractors with low hours would be good options if buying used. Any kubota, new or used, is a good decision. Kubotas are workhorses and you just can't beat them. if you buy a tractor new, don't make the mistake of buying the economy models like those kubotas you mentioned. They trick you with a lower price and these tractors aren't as capable as the nicer ones for a few grand more. I made this mistake with my current tractor. loader lift is half of the better series, and there is only 2 speed hydro, poor hydraulics, etc. Kubota is the same. Buy a B 20 or 30 series or a Grand L40 and you will be much happier. I don't know anything about skids as I have never owned one so can't help you there. I hope this helps in your decision. When looking for tractors you should look for used models on craigslist or ebay being sold by "joe landowner" who has a couple acres and his tractor is a few years old and basically new with like 100 hours on it and in perfect condition. You may get several grand off the price of new by buying one like this.
too much stuff