I appreciate the feedback from both of you. I didn't realize a better oil pump could potentially have an effect on oil temp. I have the S&S oil pump in my bike now.
After some feedback on the unit from a few others sites, I did purchase the oil bud last night. I wish I would have seen the post about those Big Sky fans are I would have at least done some more research first. It does makes perfect sense to have that airflow, just like it matters for the motor. I'm sure the oil bud will serve it's function, but it was definitely more than 60 bucks.
Between the head fans, Baker +1.5qt oil pan, a good tune, and the oil bud, I think the bike will stay in check. I ride about 20,000 miles a year and as mentioned, the bike will never have another owner so no problem here investing. Overkill? possibly. I've had some not so tactful feedback other places about adding all of this and I'm sure it's silly to people here, too. But we all have our means for peace of mind and I'm happy the beast will be cool under the not-so-friendly conditions.