That's ^ what I meant by stretch/pull/massage, much better explanation than mine - I forgot about the squeezing and dropping into the well part. Also, a light push up on the valve stem before you inflate will help prevent the tube getting pinched under the tire right there.
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1989 Schwinn Paramount OS
1980 Mclean/Silk Hope Sport Touring
1983 Bianchi pista
1976 Fuji Feather track
1979 raleigh track
"I've consulted my sources and I'm pretty sure your derailleur does not exist"