Reading up on 351w engines lately for a build I want to do, I've discovered that it's relatively easy and not super costly to build a 408 stroker that will make at least 450hp on 87 octane and will also be durable long term (as compared to say, a 347 stroker.)
Windsor blocks have their own share of issues too but yes they are a lot more cost effective to build and can be very potent.
Re: towing/race use of a 302 - Yeah, I agree, stock for stock in the same model year, a 400 will blow a 302 away towing. The 302 will win by a mile for overall gas mileage, and truly, given the right combo of fuel delivery, transmission and gears, they are not a bad engine for a tow rig either.
I hauled a lot of the same loads behind both my '86 F150 with 3.50 gears and an EFI 302, and my old '85 F250 with the 460 and 4.10 gears. Either got the job done, the 460 had the obvious advantage right off idle at low RPM but the 302 had more snort higher up - and I was not afraid to let it wrap up a lot more than the 460, either. A set of airbags, trailer brakes and slightly deeper gears would make the F150 a pretty potent tow rig. But like I said, if you vary model years much, it becomes very unfair - take an older F150 with the same 302 and a carburetor combo that's rated at least 50hp less and it's just a turd.
I like the FE engines for the same reason you like the 351M/400 - they have a ton of low end power. Plus a lot better aftermarket support as they were used for a longer period of time. They are definitely very heavy and not very economical, though - best I ever got out of my dad's old '76 F250 was about 9mpg.