second Question first: poorly, as the t-90 was designed to be installed behind 4 cylinder engines. I helped a buddy install a buick v6 in a willys Jeep with the t-90. (yes we rebuilt the t-90 with new bearings, a small parts kit & a new 2-3 synchronizer assy. First) the tranny did hold up ok behind the 225 dauntless v-6, but a Chevy 4-speed (sm-465 for example) would have been a much better choice. How well do you think your 40-50 year old t-90 hold up to a Chevy 350??
first Question: in a nutshell, a Chevy v-8 flywheel with a Chevy pressure plate assy. With a clutch disk for the t-90 of the appropriate diameter for the pressure plate you are utilizing.
Throw out bearing: try the original tob for fit and function. If it doesn't work, try the Chevy tob. This can be done "on the bench" before installing the engine/trans assy. You should do all Of the assembly, fit and function checks of this modification before Installing the engine/trans into the chassis.
Pilot bushing: get one for the Chevy flywheel, but do not install it. See how the pilot bushing fits the nose of the t-90 input shaft first, it will be too small. Ream it to fit properly, then install it into the flywheel.
Your adaptor, if correct for this swap, will set the transmission at the proper distance aft of the flywheel so the input shaft will not need to be modified,.....unless they provided a new input shaft. If so, check their tob and pilot bushing recommendations for proper function and fit before proceeding.
Bell housing: you will be using a Chevy bell housing, so use the Chevy pickup truck throw-out arm and you will need to modify or fabricate some linkage to work with your Scout linkage......or go hydraulic clutch linkage.
Don't forget your speedometer cable and backup light switch & wiring.