It seems you got a handle on it. I replaced the big main drive seal earlier this year and when I did the job I didn't replace the spacer behind the pulley, had to go back in and redo it again as it still leaked.
When I did it the second time I replaced the spacer and opted to put a new locknut on the pulley, I used the Jims meganut, there is a similar design by 3guyz that is allot more reasonable priced.
http://www.3guyz.com/vtwin-motorcycles-topmenu My oem lock plate showed signs of movement, I hate dealing with that big nut. I also went with the OEM inner primary bearing and S&S race as my baker primary bearing left a mark on the shaft.

I'm just giving you my real world experience. The price of the tools will still be cheaper than paying labor to someone else to complete the job.
Good luck, I'm sure you got this
I got a baker DD7 in my ride.....