Mike - I see that you have a SERT. If you have a copy of your map, why don't you try making an adjustment to your Cranking Fuel Table. From my experience, black smoke at start, you reduce values in the high temp area of the table, if you don't smell any fuel add to the values. Based on what you are saying, if the quick run, start button trick works most of the time, I'm guessing that you should reduce the values in the table. I changed the 80 C value to 16.1, the 96 C value to 14.1 and the 112 C thru 160 C values from 20.0 to 12.8.
I have the 103 w/255 cams. Hot start problem was awful! The hit run and then start button trick, probably worked half the time for me. I was riding with a buddy the other day, 82 deg. and hot. Got stuck in traffic for a 3/4 hour and needed gas. Engine super hot. He's been with me in the past and seen my hot start problem. He could not believe how easy it started. He was amazed. Stopped a couple of more times, engine started instantly.
Just trying to help from my experience. I went thru this same hot start problem and wasn't getting any help from local dealers or local experts. I got a lot of that's normal and they all do it, you need CRs. I would have probably done the CRs, but a friend did and it didn't help his hot start problem. Searched the Internet and also looked at new Super Tuner maps for similar builds with 255 cams. Between the two, that's where I got the idea for the change. May be worth a try for you. Takes less than 1/2 hour to load the map and try it.