A little poll for airplane owners...

The happiest day of your life as an airplane owner was

  • the day you bought your first airplane.

    Votes: 20 64.5%
  • the day you bought your last airplane.

    Votes: 8 25.8%
  • the day you sold your airplane.

    Votes: 3 9.7%

  • Total voters
    31
That’s what the monkey was telling everybody. I wonder if that’s why he disappeared?

Maybe. But then again, he’s with midlifeflyer now, so, kinda blows that theory outta the watah.
 
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I saw her first at Oshkosh 2014. She was/is my first and only airplane that is all mine. There she was sitting next to a freshly restored 275 Stearman, a recently restored 450 Stearman, a freshly restored bird dog and a recently restored Waco. It was a magical time for me. My one and only trip to Oshkosh and I was on the inside looking out. Wow. All the other aircraft were just blurs for me. My eyes were on my airplane. Bam! Dream come true.
I did it! Thanks.
 
Yeah, ok, I get all that. But the question in the OP was specific about the happiest day of your life “as an airplane owner,” not happiest day of you life. So, regarding OWNING an airplane, if you have any happy days as the owner of a machine that lets you change its oil, which day was your happiest? ;)

Numerous. First landing at OSH, passing three checkrides for ratings in her, and a few rare absolute squeaker landings, taking my younger sister up for a ride, taking disabled kids for rides through a charity that does that, taking a local news reporter up who’d never been in a light aircraft, landing on various grass strips the rentals aren’t allowed to go on... even the AstroTurf runway in Calhan, CO... first flight above the clouds on an IFR flight plan, messing around showing off the STOL capability for a small crowd of POAers at Gaston’s, numerous flights to PUB for burritos with my sweetie... all of those come to mind as highlights.

Many of those could be done with a rental, but not all.
 
Happiest day in aviation for me was the 2nd-last day of my 2008 19-day west coast adventure in the club's old 182.

On the trip, I had seen numerous beautiful sights from the air: Mount Rushmore, Crazy Horse, Devil's Tower, Mount St. Helens (and lots of others up there), Crater Lake, Grand Canyon, etc. I had taken a mountain flying course and landed at some beautiful backcountry strips. I'd landed on "One Six Right" and at the lowest airport in the US, Furnace Creek. I'd spent time with my family in Sunriver, OR and some great friends on the west coast. My friend Sheri (also a pilot) had joined me for the Oregon to Colorado part and this was her last day with me, as well as my last day of seeing beautiful sights before flying home over the relatively boring terrain of eastern Colorado, Nebraska, Iowa, and southwestern Wisconsin.

On that day, we took off from Bryce Canyon, made one more loop over the beautiful "hoodoos" there, and headed up into Utah. We flew over the San Rafael Swell, a geographic feature I'd admired greatly from the ground, and the rest of the stark, barren beauty of Utah. We flew into Colorado, where the vegetation is much more prevalent, past Aspen and Mount Elbert and the other fourteeners, and landed at Leadville (the highest public airport in ConUS).

We were on the last leg, from Leadville up over the Dillon Reservoir, through Loveland Pass, following I-70 down toward Denver and watching the setting sun create some amazing sky art on the side of a giant thunderhead south of us. The trip was coming to a close for the most part, sans that last day of flatland flying, and I just felt giddy. It had been an excellent learning experience, a lot of fun, and I got to see an awful lot of the most beautiful sights GA in the US has to offer. I've planned a thousand fantasy flights I haven't taken, and I love to plan flights, but to get to execute one with so many bucket-list experiences and have it not only live up to the fantasy but completely blow it out of the water was immensely satisfying.

BTW, that was pre-iPad and pre-ForeFlight. I bought all the charts, plates, and A/FDs and did it all the old-fashioned way (well, there was a Garmin 430W on board for actually flying it, but...) All of that paper cost me $225 and filled two grocery bags!
 
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