I've found the Digital Dipstick to be accurate enough for it's intended purpose. I've had them on two different bikes...an '06 SEUC and now the '11 SERGU (two different versions of the dipstick), and have cross checked with the original non-digital, and found them to be the same. I totally rely on it now to accurately tell me the oil level in my bike. However, I only read it when the bike is fully up to operating temperature (oil temp >200 degrees), sitting on level ground on the kickstand, and it's sat there for about 5 minutes to ensure all the oil (that can) has drained back down into the crankcase. 9 times out of 10, I do this when stopped for a gas refill.
If your bike met all those conditions after the HD dealer changed the oil, and the digital dipstick read high, I'd say they put too much oil in. When draining the oil, you can never really get ALL of the old oil out of the bike. If you just dump 4 quarts of oil in, it's likely to be too much, by a small margin. Some motors don't like to have more than 3.5-3.75 quarts in them...they'll just puke the excess out the air filter until it reaches it's state of equilibrium. My '06 liked less than 4 quarts in it, so I let it stay one tick down on the digital readout. The new bike seems to do fine full. When I change oil and filter, I put about 3.75 quarts in ( I just eyeball the bottle), crank the motor, let it reach OT, shut it off, check it, then add a tad if needed.
You should ask your dealer for a replacement dipstick if he says it's off by a full quart. Bet that will shut him up quickly.