The first problem is that the driveshaft will almost definitely not be the right length. You must have at least 3/4 of the yoke slid on to the output shaft of the transmission. If you don't, you will have severe vibration that will not only ruin the u-joint, but will also cause damage to the tail housing, the yoke bushing, and possibly the output shaft.
The second problem is that the transmission will likely not match up to the crossmember properly. You can overcome this by welding 1/4' steel extension plate to the crossmember to reach the transmission mount location on the transmission as long as it is only a few inches off. If it is more than two or three inches off, you will need to either move your crossmember (which will involve frame channeling or boxing, or you will have to have a custom crossmember built.
Third, and this is the biggest problem, is the kickdown linkage. A powerglide's kickdown mechanism is rod driven, not cable operated. You will need to custom build a rod to match up to the throttle body, not to mention figure out a way to connect the rod to the TBI.
Fourth, you will have no speedometer, no cruise, and a host of other potential problems because the VSS (Vehicle Speed Sensor) will not be present any longer.
The short answer is, yes, you can make anything work, but it will not be a direct swap.
The biggest question is why in the world anyone would do this. The only thing a powerglide is good for anymore is drag racing. But based on the fact that you asked whether it will fit behind a weaser 260 makes me wonder if you are doing it for that reason.
If you are trying to get away from using the 4L60E overdrive, a much better solution will be a 700R4 from an '88 or later 2WD truck. It is a much closer swap and will only require slight changes particularly with the VSS configuration. Everything else is a direct swap.
As far as gear ratios go, the 700R4 has a much better 1st gear ratio than a powerslide. (3.08:1 vs. 2.76:1).
If you are still bent on not using an overdrive, a TH350 would be a good alternative. They're cheap, powerful, and much easier to put in. BTW, you'll need to find one with a 9" tailshaft out of a 69-86 2WD truck or a 69-76 B-Body car. The kickdown is cable operated and I believe you can get adapters to compensate for the VSS problem.
Sounds to me like a lot more work than it's worth. Used 4L60E transmissions can be had for a few hundred bucks at the salvage yard. Probably less than you will spend or modifications to make something else work and certainly less time.
Yes it will fit, it is exactly the same as the 1992, but the 1995 is a 4l60E, which means it has electronic shift solenoids, instead of hydraulic ones so you'll need a standalone transmission computer from TCM or transplant a motor too and take the PCM from the 1995.
what other years trans will fit a 1995 cutless sup. with a 3.1 motor in it
NO
Yes. 91-96 impala, roadmaster, caprice, and fleetwood rear end are all the same and will fit with no modifications.
No.
Yes
All except the front fenders, hood and front clip.
Yes it should.
Yes, but will have to change the headlight too.
will 24" fit my 87 caprice
Yes, it will definitely fit.
Will a 1996 4l60e 4x4 trans fit in pace of a 1995 4l60e 4x4 trans