Jared, the 182 is both a "reasonable trainer" (not commonly used because it's high performance, but it'll do the trick) plus a great first airplane to own. Get your private and instrument in it, fly it around for a while, and you'll be in good shape to upgrade once you actually need the six seats. Plus, Van Bortel will have several 182s for you to look at. If you absolutely can't live with a 182, get an SR22, but ONLY if you take all of the COPA training and get real comfortable with the idea of pulling the chute if and when the time comes. I don't think there's a good six-seater that fits your mission that would also be good for training in. @Ravioli, read the mission parameters the OP posted. No, this is nowhere near 135 territory, nor does it require a commercial ticket. It's pretty much a textbook case of "incidental to the mission" as the OP has clearly stated he'll drive if needed. OP, what Ravioli is referring to is this: If you get paid to fly the airplane for your own company, you need to be a commercial pilot, not a private pilot. If you start hauling passengers around for money, that makes you a charter operator and requires a Part 135 air carrier certificate (which is quite an undertaking to obtain). Learn the rules about "compensation or hire" in great detail, including reading the legal interpretations the FAA has released, and follow those rules and interpretations to the letter, and you'll be fine. That means don't take your clients for rides in the plane, don't take other people from your company with you, don't ever call yourself a "company pilot", and don't schedule meetings you couldn't get to without the plane.