Thanks guys, I felt the cage-rattling but was out on a trip and didn't have all my resources with me to provide a full answer.
@TCABM already quoted one of the pertinent regulations about Lead Radials.
There are three cases requiring lead radials:
1. More than 90 degrees of turn onto final.
2. On an ARC but the DME source is not the same as the source for final approach guidance.
3. If an initial segment starts outside of the Localizer service volume, in order to make sure a false localizer course isn't followed, but only if the flight check is unsuccessful.
The first two are simply a "heads-up" to let the pilot of a single-VOR receiver-equipped airplane know that it's time to switch it over. It is NOT a calculated turn point. It does NOT change anything in the obstacle evaluation. In fact, it really is simply added as an afterthought, meaning all the design work is done, a lead radial is necessary, so (math math math, 2 nm, math), boom, there it is. No evaluation took place in the selection of a "good" lead radial, or accounting for aircraft speed, or anything like that. It's pure math for a 2nm lead. It means NOTHING to the design of the procedure. And I'll repeat - it is NOT an indication of where a turn should begin. That's up to you, the pilot, to determine via whatever means you like (or letting the GPS/FMS do it for you). It's literally just a "hey, you're getting close..."
I believe that the RYN procedure falls into the third scenario. The fix JIPSY is about 32 degrees off centerline, meaning it would be outside of the localizer service volume since it's past 10 nm away. I have no evidence to support that this IS the reason right now, but since it isn't an arc and isn't greater than 90 degrees, it's all that's left, and it seems to fit. HOWEVER, this lead radial was established in 1985, so I have no idea what the rules were back then or if they were any different.
HOWEVER again, according to the old source documents for this, the lead radial was simply added in 1985 due to "pilot requests". Whether they were having problems with a false localizer course, or something else, I cannot determine.
The reason the note applying the LR to JIPSY and is on the Jepp chart and not the FAA chart is one of charting convention. The question really is "how does Jepp know it just applies to that segment?" The answer is that on the source document, the lead radial is specified on the line with the route it applies to.
View attachment 116051
There is nothing on the source document (and there is nothing in the TERPS regulations) saying to "Chart this note", so it's not on the FAA chart. Jeppesen took it on themselves to chart it based on the information on the source document. I can't argue with that, it definitely makes it clearer.