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You can get away with a WR TL and a 2.88 rear - it will take a little extra attention on starts but it is definitely do-able. For a performance gearing a first gear multiplication factor of 9 is pretty nice.
I'm a little more familiar with GM Muncies and a 2.52 WR Muncie with a 3.08 rear was not uncommon and has a first gear ratio of 7.76. A WR Muncie and a 3.31 was definitely a common set up and that gives a first gear multiplication factor of 8.3. An early Z-28 with a CR Muncie and standard 3.73 rear had a first gear multiplication of 8.2. The Z-28 with 3.73 was always know to be a little weak off the line but then it gives up over 100 cubic inches, 100 HP and about 600 lbs to a Cobra. My 66 427 Corvette runs a WR Muncie and 4.11 rear for a first gear multiplication of 10.4 and it's more touchy to drive in traffic than my ERA. Second gear starts in my ERA are really not a major problem and the second gear multiplication factor is 6.4.
So it's not an impossible or even extreme gearing - just a little out of the mainstream. I think the biggest issue would be that with a 2.88 rear and only 4 gears, the rpm drop between each gear shift is going to be quite a bit more than with a 3.31 or 3.54 rear. When you shift the rpms are going to fall way back down. That will be a drawback on that winding, twisty road you showed a picture of earlier. And driving around town in traffic you will just about have to stay in 2nd or 3rd to keep from lugging the engine or getting into a trailer-hitching, jerky situation due to the low speed engine lope.
Sorry to confuse you even more.
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