I took about one year.
8 months on the 365. The Mondial found me, but it was probably a two month deal. Been looking for the right 308 for more than 18 months now.
Spook64, Unfortunately my father passed away in 1997, but I know what his reaction would have been: "Another smelly old car." He never looked back at cars he had owned. He used to have a 40 mile drive (mostly on deserted country roads) to and from his office (boy, the good old days) and when he found that he could make the trip in about the same time driving a Mercedes 300SEL 6.3 as with the Ferrari he opted for the comfort and A/C over performance. He liked fast cars (drove a BMW 540i with 6 speed when he died in his seventies) but old cars had no attraction for him.
Erik: Sounds like something my deceased father in law (83 in 2002) would have said if he had seen my 330. Your dad did have some nice classics with the 330, the 911S and the 300SEL. I recently saw a 300SEL 6.3 at the shop where I take my car - local Mercedes club officer, car was "concours."
Almost a year of full time searching. I no longer work, so I spent most of the day checking Dupont, Trader, Web, etc etc. Got exactly what I wanted. Life is short. Never compromise on things important to you.
With all the resources today, I can't see it taking 6 months as many have posted unless yout just affraid to pull the trigger. If it took me more than a couple of months, I'd compromise and never look back. Times a wastin.
Most of the fun is actually in the hunt for the right car. Also, even with all of the tools available, if you have your mind on something specific, you sometimes have to wait for one to come to market, rather than being able to sort through three dozen choices.
If you're looking for a vintage car, and don't have big funds, finding what you're actually willing to buy generally doesn't happen right off the bat. It's probably easier to find a very desirable vintage model such as a 275 GTB, Lusso, etc., because these cars have been considered classics for a long time and have had better than average care, and have been restored or reconditioned in many cases. For the bottom feeder, I think it's actually harder to search out and locate a decent vintage 2+2 than it is for the man with substantial funds to find what he wants. Many 2+2's have been severely neglected, abused, picked over for parts, and so on. I know, I've been there and done it.
About 20 years. The love affair started with Magnum, PI in the early 80's, when I decided any red/tan F-car would make a great 40th birthday present if I lived that long and my priorities didn't change over time. Made it safely to 40 in 1999 (the time flew by quickly). An afternoon of web-surfing found a nice TR for sale in Chicago. Went for a test drive a couple weeks later. As I walked around the dealer lot still wanting to make sure I was making the correct decision after waiting so many years, I came back full circle to the TR still idling outside the dealer's garage door entrance, practically begging me to take her home with me. I signed the deal that afternoon and had the car delivered a couple weeks later. The car will stay with me until one of us gives out, since I don't trade vehicles...