or, if the seattle trip is a couple of times a year, make it one longer day with a stop or two (8-10 hours door to door) or make an overnight part of the tip somewhere fun (Wyoming/etc)?
Looking at Southwest. it's an 8 hour flight with one layover. plus TSA time/etc. it's probably about a wash door to door vs taking a 56TC or similar. It'll cost more in your own plane,a nd your chance of making it are lower, so it all depends what you prioritize. I agree. I'd by for your 95% mission and then either take a longer trip for the once in a blue moon, or just fly the airlines. For example, i'm considering 160-200kt aircraft that would be great west coast planes, or even to the Midwest. The flight to the gulf coast though, would be like 9-10 hours. I'll do the same thing and weigh airlines vs my plane. Figure it's 250/hr or so for variable costs on a twin (perhaps less) X20 hour round trip = $5,000 in variable costs. COACH tickets for my family of 4 during any school holidays are about $3,500, and the door to door time is about the same as the airlines (always has a layover somewhere), so it's a wash for me as well.
what i personally wouldn't do would be jump into a 300kt plane at 150 hours both from a safety and cost standpoint. at $150k purchase price though, he can easily get a 95% of mission plane, and decide on a trip by trip basis if he wants to use airlines or fly himself.