For our flights to Europe from the USA in the Lear 60, Jepp was superb in every respect from flight plans and slots to ground transportation, hotels and fueling. We were able to charge many of these things directly to our Jepp account. While in Europe we'd typically fly several legs to different countries, so this service was highly valued. We always had slots and everyone knew when to expect us.
The major hurdles in preparing for the first trip involved making sure of the necessary documentation. MNPS, RVSM, RNAV, 8.33 Khz, FM immunity, Enhanced mode S and the list goes on. The SAFA checklist is very handy too. NAV database and paper chart revision cycle timing with your trip is worth looking at in case you need to make any special provisions to receive updates.
As for the actual flying, there were few surprises. We had done the Air Training International IP course online recently, so the oceanic procedures stuff was at least pretty fresh in our minds for the first trip. Going random route from Goose or Gander, I recall getting our oceanic clearance on the ground. Same headed West out Shannon. Check the HF before leaving home though. I was glad we did because the antenna coupler needed some work.
Once in Europe just remember to take note of the TL/TA at each airport of arrival/departure. We wrote it down on a piece of paper and taped it on the instrument panel. I had read that this is the source of a high percentage of level busts recorded by Eurocontrol. Expect parking to be in remote areas of European airports and van rides necessary to reach the offices of your handling agents. No FBOs in the sense we're accustomed to in North America. Some countries even make you go through airline style security to get to your plane like they do in Mexico. Plan LOTS of extra pre-flight time at the airport. I suggest informing owner pax that they can expect big delays due to lost slot times if they show up late too. Sometimes you can get a new slot pretty quick and sometimes you're just out of luck.
And lastly, remember that bit about calling Canpass BEFORE taking off from the last airport prior to re-entering Canada! It seems to be the one sure way to upset those guys. They cut us a break for calling them via Satcom 2 hours out but issued a sternly delivered warning nonetheless. (thanks eh?)
I hope you get a clear view on at least one of your crossings.
westhawk