It is tough to say. The vacation property/home market was down 30% in 2007 (according to the NAR). It is impossible to predict what is going to happen moving forward - but my guess is that the deals may get even better...of course the problem with that is your dream property may be off the market by the time you feel the market has hit bottom.

There are a lot of great deals right now - if you are purchasing a property to use it, and not flip it, I would buy today.

As you know - we do get snow in Northern WI - lots of it. How difficult would it be for you to detrmine the quality/condition if there is snow on the gorund. I say look now - do your homework and research the areas you know you are interested in. When winter comes around, if you haven't already found something, you will be well educated on the market and locations. Don't always count on lower prices in the winter. Each property is individually owned and therefore may have different circumstances attached.

I'm assuming that at this point in time you have nothing specific in mind. If that is the case, the only advantage that I see it that you may have less competition for a property and therefore perhaps could get a better price. If you are borrowing for the purchase, and interest rates are important; today you know what those rates are. Tomorrows rates you do not know.

If you do have a specific property in mind and you don't act now, you'll risk it not being there in the winter.

Depends on where, and for what purpose. You should probably check it out whenever access is easier. If your primary goal is summer usage, you should definitely look now, to be sure you get the features you want!