Overdrive or don't worry about it? !

Last time eh....yeah the check is in the mail. If you are a serious enthusiast
You will always be building something new, even if it is in your mind.
Drive the piss out of it. YOLO. Sure your engine will wear out quicker, no problem, but $300 inparts to refresh it.
Find out out what will be the most pleasing to you. Then make changes. Most of what I’m doing is cruising, some spirited road driving, and stoplight to stoplight. If I want a long term cruise I’ll drop the 2.76 in and take the 3.91 out. I’m guessing that by the time you fit an OD in the car you’ll spend $2500. 2.76 and 2.94 are cheap you should be able to get one for under $100. Check out some tire/axle/rpm calculators