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can you just redrill flywheel to new diameter?
That's the idea - and buy the correct flywheel bolts.
At 245k I figure it's going to need to be rebuilt soonish, so might as well do it now before conversion while the rig is out of commission.
Thoughts?

I know there are differing opinions but it seems like the 2FE still does not have the added 20HP of 3FE. this is my main reason for not doing 2FE. Also it may seem trivial but the bolt on accessories on my F2 are all old and needing replacement (PS pump leaking, alternator low output etc) while the accessories on the 3FE engine I am getting are all 2-4 years old and in good condition.
Plus my 2f block is an '82, my understanding after some research is that the pistons on pre '86 fj60s are different and will not work with 3FE head.
also I am hoping to get a few hundred bucks perhaps for the 2F core. If i do the 2FE i will have a 3FE bottom and 2F head which is pretty much unsellable.
As someone running a 2FE, and picking away at a FJ55 trail truck project with a second 2FE......
A 2FE has more power than a 3FE, which itself has more power than a 2F. A 2FE is a stroker version of the 3FE. A 2F head on a 3F block would be underwhelming, you would lose displacement and compression. If turbocharged.....maybe.
Is your engine out of a FJ60? If so, it will have flat top pistons and be compatible with a 3FE head.
My non-binding vote is find a good running 2F someone has pulled for a V8 or diesel swap, pay $500 for it, drop it in for cheap, and drive on. Paying a shop to work through all the little issues of an oddball swap (that’s what a 2F to 3FE or 2FE swap is) won't make cents. If yo have the skills and drive to take on the swap yourself, sure
X2 on staying 2F.
The best way to do a 2FE or 3FE swap is to have a donor vehicle from which to pull parts because of the small items that are often needed.
What do you guys think of the cruiser parts.net 3FE conversion kit they sell?: 1958-1987 EFI Toyota Landcruiser Conversion Kit