Displacement matters, even in a boosted application. More displacement will make a given turbo spool up faster which makes it much more responsive for street driving, or alternatively, more displacement will allow you to spool an even larger turbo at a reasonable RPM. However, I fully agree that the return on HP/$ is much better with boost than internal mods. That said though, boost multiplies any gains naturally aspirated, so a stroker will have much bigger horsepower gains with forced induction than naturally aspirated
Tall deck windsors are a lot stronger than short deck Windsors and not particularly fragile for realistic street power. Richard Holdener got 1,047HP and 1,030ish FtLbs. @ 23PSI out of a stock junkyard 351 bottom end with some ring gap.
Even the worst 335 series heads are better than the best factory Windsor heads, so I wouldn't say they have a breathing problem. The closed chamber 4V heads flow as good or better than some aftermarket Windsor heads.
Not really oddball, Ford just didn't use the tall deck 335 engines in performance applications, so they never got much popularity with the hotrodding crowd. The 351M and 400 are essentially tall deck clevelands.
The 351M is a destroked 400. It has the 10.3" deck height like the 400, not 9.2" like the Cleveland. When I looked into it someone had a ~434ci stroker kit for the 400/351M. People build 408 Windsors regularly with a 9.5" deck height, so I see no reason to think a 400 is near it's limit considering it has an extra .8" of deck height.
A built 400 would be