I flew along with a couple of owners of a 340 who were both fairly high time pilots but who needed a CFIIMEI along to fulfill insurance requirments for a specified # of hours. I had more time than you (well over 2,000 and an ATP with 400+multi). We happened to not have any passengers on board. There was another instructor who also flew with them for some of the hours and he had a lot of 340 time. The ironic thing is that there are situations in which a properly rated CFI can fulfill insurance requirements for owner-pilots but not himself be insurable, or be insurable only at a very high premium, if he were to try to rent or simply fly (say, on a shared expenses Part 91 basis) the very same aircraft for his own personal use. Many policies also have an "open pilot" provision, and you may be surprised to find that you yourself might not qualify and would need an instructor to fly with you. However, despite all this, you STILL might qualify as a ride-along instructor. Actually, from the insurance company's point of view (and maybe the passenger's?) you probably will be the PIC, as the owner is not insurable on his own yet. In any event, double check with the insurance company, or have the owner do it, to make sure that you and the operation are covered. You have 2 or 3 potential claimants here: the owner, the passenger, and possibly even the insurance company itself. Might even want to get your own CFI policy, if you don't already have one, and see if it covers you for this operation. True that test for 135 is generally comp or hire. I haven't checked to see if there's anything special about donations to candidates/political parties. (By the way, are you being paid?) The 340 is an enjoyable airplane to fly.