My father and I started building kits together when I was about 5 years old in 1958. One of the first ones I remember was the old Monogram box scale PBY. I kept it for years, even though it shed most of the detail parts (landing gear, engine cowls & propellors, etc.) along the way.
The first kit I remember really doing "on my own" was the Monogram 1/48 F4F.
(My father had been a 3rd class petty officer/avation metalsmith in the Navy and was my "resident expert" when it came to building all the old Monogram 1/48 WWII carrier planes - he had patched holes in all of the real things during his time in the service).
Some other personal milestones:
The first kit that I ever painted was the Monogram SB2C, which I built when I was in third grade. I used Testors gloss enamels to brush paint the interior green, the undersurfaces gray, the prop tips & the dropable bomb yellow. Hand painted all the canopy framing freehand. Left the uppersurfaces in the molded blue plastic. It was a big milestone for me at the time and I was very proud of it. I also remember breaking off one of the prop blades and I was never able to glue it back on so it would stay.
The Revell 1/196 USS Constitution also sticks in my mind. I built it around 1965 and remember spending seemingly countless hours working to get the rigging right, adjusting the tension so that it didn't distort the masts. It came out well enough that my parents asked if they could put it on a shelf in our living room rather than hidden away with the other models in my room. It was still there when I left for college, but it didn't survive when my parents moved a few years later.
The first kit I ever spray painted (with a spray can) was a AMT 1964 Impala that I built for a contest at a local hobby shop, probably around the 1965-66 timeframe.
My first airbrushed model was a Revell 1/32 F-14A Tomcat back in 1982, using my new Badger 350 and a spare tire as an airsource. I mixed my own light gull gray and every batch came out a bit different shade/texture.
One of the "failures" that sticks in my mind was the Monogram Phantom Mustang that my grandmother gave me for Christmas in 1962. I could never get the main landing gear to work without binding and as a result never glued the completed fuselage to the wing/base assembly. I put it aside in frustration and never went back to it.
Mark