Steve can bend my ear anytime.... he's got my email!
Have been following the same discussion on a number of boards - and he's received a lot of good advice already....
If I had to pick just one thing - it'd be the deep discount specials.... keep'em to once a year (if at all).... he's trained his customers not to buy on an ongoing basis, and while he get's a lot of work with the specials, it's at a much lower margin than he needs...and there's an inevitable dry spell after...
If it was me - I'd do the following...
1) have a simple (from MFG/delivery standpoint) high utility introductory product at a lower price point.... like a block plane... 2) Sell planes with a re-order coupon for a discount.... valid for something like 3 months... 3) Try and make more small runs (and put a small discount on those (to reflect economies of scale... say 10%)), instead of soliciting too much custom work... and put a small premium on the custom stuff...Not much else I could add without knowing the ins and outs of his business....
Making a living off your own labour is a tough thing to do.... no matter what it is you do. Many undervalue their own work, usually by undervaluing time, or not paying as close attention to how much actual margin an activity generates (as opposed to how much gross sales are)...
Cheers -
Rob