I am running the TJ Products lowering kit with Heavy Duty Lowering shocks on my 2000 Road King Classic. The TJ kit does not affect the shock angle so you should not have a problem with hard leather bags, TJ kit is a little more expensive than most (got mine used on ebay). Never had a scrubbing issue until I lowered the front 2" with Progressive Drop-in kit. Now I will scrub just barely when I hit a large dip in the road. The more air pressure I run in the rear shocks (now @ 25 psi), I don't seem to have this issue since it barely scrubs. 2 up may be a problem as me & wife have not rode together since lowering front end.

 

Upon removing my wheel and tire I too noticed my tail light wires rubbed - but they are sticking OUT 2 or 3inches! So I don't see that being too much of an issue. With my Chrome Lowered Airshocks I can always lift it back up!

From what I am reading I am going to do it and keep an eye on it. Again... were only talking about 2.5" not 3 or 4... So that can always be brought back up with a little shot of air.

 

I did it with the Harley lowering shocks and really well made bracket.

It looked awesome but bottomed out.
I ended up having to replace my oil pan.
I hit a pot hole that would have been no problem other wise and cracked the pan.

I ended up going with 11" progressive 440's and was very happy with them. Never had a problem even when 2 up. I think they ride a lot better two.

If you do it make sure you lower the front and again I'd use the progressive lowering springs to slam your bike to the ground, look awesome and get the best ride out of it.