Well, I'm not the expert here, but aren't crude stocks somewhat irrelevant to a heating crunch?  Isn't refining capacity the limiting factor?  We burn fuel oil, not crude. Also, a relatively  small percentage of heating is accomplished with oil.  When it comes to heating, natural gas is the bigger concern, and North America is already in decline there, so that's where the shortage concerns come in.
Check the DOE/EIA page at http://tonto.eia.doe.gov/oog/info/twip/twip_distillate.html for lots of information on distillate stocks, refining, imports, etc.  A quick scan of the numbers and graphs on that page seems to show that we're in slightly better shape now than we were a year ago, thanks in no small part to imports and what appears to be a relatively quick refinery recovery.

In general, I think Khebab has a good point, though--there's certainly a track record of people seeing higher prices and jumping to the conclusion that shortages and chaos of Biblical proportions are just around the corner.

The season I'm concerned about is next winter, not this one.  Between Iraq, China, India, the Caspian Sea basin, and another hurricane season, there are just too many unknowns for my comfort level.