Personally, I like the styling of the 67-68 the best. The 69 just looks to big for me, and they just got bigger after that. A lot of cars are like that. The 65-66 are very nicely styled too, but not very aggressive looking.
First off dont let the talk about 20 to 40 grand scare you off... I just purchased a 66 coupe for 5 grand and it was in pretty good shape. you can find these deals if you are persistant and a little lucky.. if it is your first car then maybe you should get one with a 6 cylinder engine.. this to will bring the asking price down..Whatever you do, take someone with you when you go check these cars out, it is easy for a seller to intimidate a solo buyer, so beware..
None are really better or worse than others per-se. They all share the same basic drivetrains and suspensions although there are differences. I would pick whatever one you like the style of best and what you can find and afford. I always liked the '67-68 because they have the classic 65-66 styling but with a little more muscle look like the 69-70. 1968 and later have some saftey features earlier ones don't have. Collapsable steering column, side marker lights, ect...
if your looking for one that is a collector a 67 Shelby gt 500 it would sell for about 1 mil.
if your just looking for a cute convertible then a 66. they made a lot of them and they are not that pricey yet . you can still get a clean one for about 10 k.
Well if you like the shoe box fenders and quarters of the 64 1/2-66 models then be my guest. My opinion is that the 67-68 looks awsome. None can compare to the 70. Hince Ford copying the 70 in the 05 model.
The only thing about buying an older model Mustang is the engines hated low octane gas. Especially the 351C they were bad for preignition. This can be worked on to fix the problem nowdays, but head work is expensive. Besides that the Cleveland stock for stock produced about the same horsepower to weight ratio as the 351W. If you have money to burn then a good "crate engine" is well worth the time, rather than monkeying around with an older design engine.
Look in the trunk pockets on each side, right behind the wheel wells on each side, that is a problem area on the mustang for rust. also if they did messy body work it might be visable from the inside of the quarter panel. Look under the car at the floor pans. It is amazing what some new carpet in the floor will hide, saving the seller lots of money fixing the floorpans.
If you are unsure about the engine, check the dipstick, most poeple don't think to top off the oil. If it is very low, I would worry about the care they give; also light brown colored oil, means they cared enough to change it before selling... The transmission oil dipstick also, even though you cannot get a good reading, you can see if the fluid is black, bad sign also, should be redish color. Brake master cylinder should be full, if not most likely leaking somewhere. Look for wet spots anywhere on, or around the engine compartment, even if it looks washed or clean. Leaks appear in short periods, faster than most people have time to wash them off. Look under the car to see any wet spots that might have accumalated in the previous days there. These things don't take away from the sellers rep, but they do give you some barganing leverage at the point of sell. Everyone is trying to make a million with a grain of sand nowdays.
if you have the donaros to buy one the best would be 1966 to1968 fastback they are exspensive but their value has greatly increased over the last several years (GT 350 or 500) and they will only increase in value as time goes on.
i have two (1968 GT 350 and 1966 with a 289)