Right now, I've got a '59 292 in my '30 Model A Coupe.  The transmission is a 3 speed toploader from the early '60s (non-synchro'd reverse).  I THINK it's the wide ratio transmission because there seems to be a big difference between 2nd and 3rd.
The rear is a Dana 41 with 4.27:1 gearing.  The tires are 29.5" tall.

On the highway it's spinning at 3200 or so at 65 mph.  In Second Gear, at around 30 mph in town it's also spinning close to 3000.  

Anyway...I originally thought about getting a 9" rear with more reasonable gearing in it, but then it may not be as fun.  Doing the math with a T-5, with two extra gears, and one of them an OD, I think it would be a better option.  

1.  What would I need to make this work?  Clutch Parts, adapters, etc.?  
2.  Anyone know how much further back my shifter would be coming from a toploader?
3.  Anything else that I'm overlooking?

My 55 TBird was born with a T86, R10 overdrive and 4.1 rear gears and still has it's original drive train. My motor is a .060 over 292 with 312 heads and intake.  It's a wonderful setup for modern driving.  I disable overdrive while driving around town as I rarely get into third gear with the O/D engaged. I use O/D for highway driving.   At 60 MPH In 3rd gear O/D, my engine is turning about 2,000 rpm.  The O/D drops the RPM by about 1/3.  The 4.10 gears make for spirited acceleration. It's a very peppy car.  I am nervous about blowing my transmission, so I never hammer it from a stop or power shift.  I blew up my share of Ford three speeds back in the day and I don't need any more of that.  One more thing, the T86 is not syncro in first. With the O/D engaged you can shift into 1st without coming to a complete stop.  The T85 R11 was a very tough transmission if you can find one.  It came behind 312s and some big blocks. I doubt you will blow one of them.