First, I must admit my "expertise"
comes from the school of early car hard knocks and I paid for my education! I do have a passion for the early cars!
The important question is how much do you have to invest?
Are you going to invest "sweat equity" or checkbook equity?
Do you have mad welding skills?
Are you patient?
IMO, current affordable top tier cars are the Ss, Soft Window Targas and the very early cars [64, 65, 66]. Sportos, Es, sunroof Ts, low mileage Ts and SWB Normales appear to occupy the next tier. Then you have the non sunroof and targa Ts.
Hotrods are very personal and can hit any of the tiers depending on detail of finish. Cars w/ pedigree [Steve McQueen's S] command very stiff premiums. RSs also occupy their own space. Factory prepped race cars orbit the earth.