The funny thing is, I think all G body 2 doors use the same driveshaft length no matter which of the 3 automatic transmissions they came with, and the yokes are the same too. As for what you have, it is a Buick engine. There is no Oldsmobile V6, only the putrid (w/o turbo) Buick 3.8/4.1 and Chevy 200/229/262 V6 engines. I would not spend the time or effort to put ANY 305, or 307 in your car. GM only made one 5 liter V8 with good performance. It was made from 1967-69 and called the 302. I would go with either a Buick 350 or a Chevy 327/350/400 and call it a day. If you really want an Olds engine, use a proper 330/350/403 or a 425/455. Skip the 307. It is not worth the investment in time or money. According to one of my Oldsmobile brochures from 1985, the HO 307 powered 442 did 0-60 in 9.8 seconds. That is with all the help the 3.73 gears, a roller cam and a dual snorkel air filter could give it. The MC SS did it about 2 seconds faster with a similar rated L69 HO 305. You may be able to get a 307 to bark, but that is only because it is a dog. Arf!
As for the electronics with the transmission, it is not a big deal. The trans will work and shift without the computer. All the computer does is control the lockup of the torque converter. There are kits out there that do this with no computer and they are not that expensive. If you live in a non-Nazi state and have no inspections, you can just chuck the computer and run a proper Quadrajet and HEI distributor like I did. If not, and you have an under hood inspection, you will want all the computer and smog stuff to run a Olds 307 or Chevy 305 (depending on which family of engines you go with), but with an aftermarket chip and slightly richer secondary metering rods. The chip will give you more total timing and the rods will allow for more secondary enrichment as the WOT is not computer controlled, only part throttle is in a GM CCC system. You will also want a free flowing exhaust that runs a single 3 in cat. Get the downpipe for a L69 Monte ( VIN G) If running a Chevy, and the after cat for a
Grand National no matter which engine you use. The GN systems tend to be better designed and have identical placement to a Monte, but some catalogs do not list them as such ( Summit being one of them). Then have an exhaust shop adapt the 3 in cat between the 2. Just avoid the Dynomax system like the plague as it bottlenecks down to 2.5 in for about a foot, restricting flow. If you order a system for a LG4 150 HP 305, it will come set up for a 2.25 in single cat and hurt performance. For the Olds, I am unsure if they used the Vette's oval inlet and outlet (conveniently a slightly smushed piece of 3 in tubing)catalytic converter like the HO 305 MC and Camaro did, so you would have to check and see. It is not a simple swap, but it is a simple swap. It all bolts together if you have the right pieces, but you need a lot of pieces to make it all happy. A good donor car is nice, as all of the little BS adds up quickly.
The difference between a 231 2bbl and a good V8 will be night and day. Couple it with a mild gear, and you will love it. There are no real drawbacks to a swap done right, with a conservative engine combo other than a little less highway MPG. The added torque will make it more fuel efficient in the city and will require less throttle to get it moving.