My first everyday bike bike was a vintage peugeot racing bike outfittedt with Schwalbe Marathon tires, fenders, lights and bike racks. Had been my fathers racing bike, then his commuter/trecking bike, and when he bought a new bike, he handed it down to me. I handed it down to my brother when I got my second everyday bike: my grandfathers trecking and winter training bike: an old Gitanes racing bike outfitted with Schwalbe Marathon, fenders, lights and a bike rack... It's still sitting in my basement, waiting for a major overhaul.
My first road bike was a 1976 Cinelli with Campagnolo super record group, handed down to me by my grandfather. Unfortunately, I had a severe accident with a Bernes Mountain Dog (which ran onto the road while I was practicing sprints). I flew more than 10 meters, frame was cracked, rim broken, derailleur cracked...
With the money the dog owners insurance company payed I then bought the components for my first "own" road bike. I researched spare parts catalogues and comparing the parts numbers, I found out Campagnolo was handing parts down: this years Athena derailleur seemed to have been a Chorus part the year before, and before that a Record... That was in the mid-90s, I don't know if Campa still does that. I had a deal with our bike shop: I would buy the parts, but had to assemble it myself under their supervision. (My parents had been customers to this shop ever since I could walk.) The shop owner insisted I gave him the cracked Cinelli frame because he found it so beautful: last time I visited them (in the mid-2000s) it was still hanging on the wall. :-)
My new bike has a handmade italian steel frame (Sancineto) and the above described happy mix of Campagnolo components. Leather saddle is still from my grandfathers Cinelli, and of course, I still have it. Have not driven it for a year because of problems with my achilles tendons, but as these have improved significantly in the last months, I might give it a try again.
Bike parts were somewhere around DM 1000,-. This would be around 500€, but if you figure in 17 years of inflation, todays purchasing power might more be around 1000€.
My mountain bike is a vintage steel frame hard tail, no suspension Checker Pig with Shimano Deore XT group (with the exception of the ight shifter, which I had to replace after a crash (commuting to work on a washed-out farm trail, steep ascent, very muddy - that obviously was a pretty dump idea) and could only manage to get a LX. Spare parts situation with Shimano is horrible, at least for older parts. Bought that bike used from a guy I met on the German Saab car forum for 250€. Have some problems with gears not "staying in gear" but jumping around on the rear cassete when exposed to torque. Either I messed up the adjustment after repacing the shifter, or chain is worn. Need to figure that out.
Last year, I bought my wife a commuter bike as a birthday present. Bought it used, of course. Scott aluminium frame, front suspension, Shimano Alivio components, Schwalbe Marathon tyres, freshly serviced. Not too bad for 150€!
She is not using it to commute (one way 25km, she takes public transport instead), but happily zooms around in town to meet her friends.