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Hi Jeremy, Good choice of model and a nice colour as well. I've done an 1850 to overdrive conversion some years ago and it went well, but there are things to look-out for.
First on the additional work you mention; if the oil in the bell-housing is black engine oil then yes it will be coming from the rear crank seal. That oil leak won't get any better so while the engine is out I'd replace it, particularly as it would be worth doing a 3-part clutch replacement as well. Fill the inner aperture of the oil seal with grease before fitting to prevent burning of the seal when first starting. The seal is Part no 143148 and you'll need the gasket as well 143845.
There are 2 types of clutch driven plate; early and late depending on whether the new gearbox has coarse or fine splines. Likewise 2 different clutch alignment tools.
You will also need the 1850 O/D gearbox cross-member and gearbox mount. The 4-speed box one is very different.
The important bit on the 1850 is the clutch fork. Have a careful look at the pivot point as they crack at this point and break. Only 2nd hand available right now, but they are compatible with Herald / GT6, I seem to remember.
Check the new O/D gearbox comes complete with the gear-lever and the O/D solenoid (£80 now) . Change the oil and clean the magnetic filter at the back. Try and get the wiring loom as well, but its not difficult to make up. Check the electrics work for the O/D and the reverse light switch on the bench before installation. It's much easier.
If you have an early car there is a slightly different exhaust centre box as well.
Replace the spigot bearing in the back of the crankshaft as well.
Don't forget the rear exhaust bracket to exhaust pipe. The bolts go into oil-ways in the gearbox so they need a smear of sealant on the threads.
As to the rest, Yes I would do the crank oil seal while its out. The crank pulley bolt is 1 1/2 A.F. but is much easier to do with the engine out. The seal is just behind the pulley in the timing chain case. Again grease the aperture to prevent burning on start up.
It would be worth cleaning off all the old oil on the engine externals with something like Gunk. It makes it much easier to see leaks but I suspect this will be the camshaft cover gasket if its on the n/s.
I don't know about a double lip seal. Maybe one of the engine experts on here can help ?
Good Luck with it,
Tony.
Many thanks certainly food for thought. Something to ponder over while I clean all that caked oil off the block. The sub frame is pretty well covered too, the whole engine bay will need to be clean before I can think about giving it a coat of paint and theres also the small matter of welding up the split on the bulkhead. I'm hoping to persuade my friend to weld it up with his Tig welder. It will make a neater job and I may get away with little or no grinding back. Not that I'm trying to put off doing the crank oil seals, but I think I'll need to build up to it.