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In my opinion, its more beneficial to upgrade that 300 than put in a V8. The modifications you would have to do are numerous to switch from I6 to V8. For instance, motor mounts, wiring harnesses, new computer (standard on almost any motor swap where you're changing sizes), possibly fuel system too, but I don't think so.
The 300 I6's have the potential to put out a really high amount of torque compared to a V8, even though you might not be able to build the horsepower that high.
Check out the sponsor list to the left for some good "goodies" for that 300 and I'll bet you could come out with a pretty nice I6.
So I guess the answer is yes you can swap a Windsor, but a lot of work is involved.
I'm near finishing on a swap. Not that bad I onlym did it because the 302 spun a rod bearing and I was given a new lightning motor. Hard to pass up a free motor otherwise sticking to a 302 would have been much easier. Most of the issues I've encountered are from my mods:
custom exhaust- Mockedup just need welded
MASS air conversion-took easy route with FR kit
Trickflow intake and BK 65 TB- custom Cable mount needed, any sources???
Smog delete- learning vacum line schematic
By far, the easiest way to do an engine swap is with a donor vehicle. Everything you need is sitting right there, you just have to move it. If the transmissions in the 2 vehicles are the same then problems will be minimized, but the 4.9 I6 and 5.0/5.8 windsors do share the same tranny bolt pattern.