The parts books say the 307 starter wiring to the battery is 60". It may be a bit less than that, but they specify that in the parts book. The negative wire going to the head shows a length of 20". I never measured them, so I'm not 100% sure on exact factory lengths. I do know they're small gage.
The crossover pipe may have to come off ONLY if it's something other than an Olds 307 with the factory exhaust.
You can do it on stands, but ensure the car is super stable and the jackstands are sized appropriately. You'll obviously have less room to work with, but it's do-able.
Once you get under there, you'll see it's obvious you'd have to be needing to change out the heat riser gasket or heat riser valve assembly to "have to" undo the crossover pipe. Or if you just don't want to drop the starter and leave it in place. Otherwise, LEAVE IT ALONE. The crossover pipe only covers up about a couple of inches of the front of the starter.
Plenty of room to drop the starter out once the heat shield is off and the 2 starter mounting bolts are out (2 fasteners on the shield, a nut and a bolt).
Granted, the starter would have to be tilted back slightly, but it should come out easily. You will have to remove the converter cover, though, and make sure the battery is disconnected. Which is super easy to do. Then drop the two starter bolts and support the weight of the starter and lower it down. Note the orientation of the wiring, and remove the nuts/washers *ss applicable and drop the starter out of the way. It's not super heavy, but don't let it drop and pop you in the head, it will hurt and you'll use language that your mother shouldn't hear. Don't ask me how I know. If you have a helper, or something you can sit the starter on while you remove the wire nuts, you'd be better off. DO NOT let the starter hang by the wiring.
I only advise taking the starter completely out so that you can route the starter wire exactly where you need it without having to deal with a starter hanging by a wire or not being able to place the wiring where you need it with plenty of room to work.
IIRC, the factory 307 starter has only one small post, the S post. This is where your purple wire goes (just in case someone put an OLD solenoid on it with the S and R posts). The fat post, obviously, is for the battery and the other stuff. If there are any shims, replace them when re-installing the starter motor.
To give you an idea of clearance, see pic below.
After disconnecting battery:
1. Remove converter cover- 4 bolts/screws
2. Remove starter bolts- 2 bolts. (9/16" heads IIRC). You may have to remove the heat shield first if it's there, see bottom pic.
3. Remove solenoid nuts- 2. (don't recall the sizes, because I'm old.) I want to say 5/16" and 5/8", but my mind is foggy on that.
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picture out of the 87 CSM:
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