"Something awkward about angling it in with the much longer spring loaded brushes with the alternator still mounted on the car. Any tips on the technique based on similar experience? "
Good thing you asked. My knee-jerk response is "practice." It fun to accomplish this without the mundane work of removing the alternator.
In other words, I've managed to do this umpteen times and seemingly not discover any useful methodology. The last time was less than 2 weeks ago. I recommend letting the car cool off some, so you don't burn the back of your hand on the preheat stove if your car still has one. My daughter's new 93 does.
Tip #1: Use a new #2 Phillips, if the regulator screws are Phillips. I prefer the slotted screws in this location, like the old ones had. The Phillips will cam out unless the bit is pristine and high quality. If they do, bring small vise-grip pliers to the screw head to get it started out.
Tip #2: Use a flashlight and mirror to STUDY the target area. You already have it out to check the slip rings, so MEMORIZE where the screws go and be sure the area under the screws is clean, as well as the diode plate contact Phil mentioned. It needs a good ground and a good D+ connection. The new brushes will provide the good connection to the rotor through the slip rings.
Tip #3: Forgo your instinct to put the back screw in first, saving the front one to find by sliding the regulator assembly in an arc around the back mounting screw. Start the front screw and between thumb and forefinger (yes this is all blind work based on your memorization) turn it in until it is as tight as you can make it without a screwdriver. Then rotate the brushes (against their springs) until the back screw drops into the tapped hole in the housing. I cheat and have a supply of new screws for these. I only wish they were Torx instead of Phillips. Or slotted.
Your brushes should look like this, but they won't after three years.

--
Art Benstein near Baltimore
Subj: How To Diaper A Baby
"Spread the diaper in the position of the diamond with you at bat. Then fold second base down to home and set the baby on the pitcher's mound. Put first base and third together, bring up home plate and pin the three together.
Of course, in case of rain, you gotta call the game and start all over again." -- Jimmy Piersal, on how to diaper a baby, 1968
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