They do make special headers that will allow you to fit a 351C into a 65-66. I know that Total Performance in Michigan was selling these headers for about $300 back in '87. John Vermeersh is the name of the shop owner, and he was also listed in the back of the FMS catalogs as the answer guru. I don't know if he's still in business, but it might be worth checking into if you don't want to cut your shock towers.
About the T-5, I don't think it will last behind the power and torque of a 351C. I bought a new T-5 for my '65, but I have decided against using it since I'm concerned it won't last behind a hot 302. For whatever it's worth, I've broken two T-5s in my '91.
If you're looking for a new T-5, I have one for sale but I don't think its a good match for your application. A Tremec would be more durable.
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'91 LX
Procharger, 3 row intercooler, extrude honed Cobra intake, Mac full Length Headers, 30# inj., 73mm C&L, 75mm tb, E303 cam, 289 rods, ported E7 heads, MSD, T-Rex w/255 lph Walbro, 5 lug conversion, Cobra R wheels, 3.27 gears and Moser Axles.
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