If you were making the trip solo, then the RK would probably be my choice. Even then I'd opt for a tourpak/trunk, as I tend to overpack. Since you're going to be 'two up' for the outbound leg, I'm still voting for the Ultra. I just did a quick check on my local Craig's List and found a couple low mile 2007 Ultras for under $18K. Buyer's market for used HD's, so don't payup at a stealership.

US 30. I've ridden it from western PA to York. Lot's of good scenery. Add a quick sidetrip through Gettysburg battlefield. There are many good two lane roads in mid/south Ohio/Indiana/Illinois. Run down to St. Louis and do the Arch, then work your way back thru Hannibal and US 36 west to St. Joseph (home of the Pony Express, and Stetson Hats). Then continue west, but instead of Denver, hit Colorado Springs, Pikes Peak, etc. Then work your way across the continental divide to Breckenridge via the two lanes. From there west, you've got lots of great scenery.
Not wanting to turn this into another 'what raingear' thread...

My mantra is: 'If you're gonna ride in it, ya might as well be dry'. Don't cheap out on the rainsuit. I recommend a two piece suit: Bibs (with boot stirups) and Jacket. Both myself and my wife have HD rainsuits, and we are both very pleased with them. We also carry/wear Totes overboots, and rubber gauntlet length 'chemical gloves' that we wear simple cotton work gloves inside (to keep down sweat).

If you go with the Ultra, which has lower fairings, you won't get the 'driving rain' on your feet. I also have a pair of clear 'safety glasses' that I wear (if it's too dark for sunglasses). Even with my big 'ol windshield, I get rain in my eyes. Which isn't fun at 70mph. All our 'stuff', including the Totes overboots, folds down and fits into the bags the HD rainsuits came with. Both fit nicely on the top of the high side saddle bag, where they are easy to get at. Speaking of that:

Practice putting your raingear on. Practice in your driveway. Practice without anything to sit on other than your bike. Murphy's Law prevails when it comes to getting wet: The next overpass is too far away. Which brings up another hint: At the first indication of rain, get your boots and bibs on. Save the jacket and gloves till later if you think it's likely you're not going to get wet. Otherwise, put it all on. From personal experience it takes denim a loooong time to dry out.

 

I would fly to Denver and rent there. The plane ticket cost would be covered by not making the trip to and from that far west. Rental price would be decreased also.
Wife and I have done some great riding on rentals.

 

Went to dealer today to get sporty state inspection. While there tested RK and Ultra. (and Heritage Softail) Liked the RK better than Ultra and like the ability to strip it down when not touring. Didnt want to ride home on the sporty... Checked ebay and craigslist as advisesd by Hackd for RKs. How far back do you recommend I could go and still get a reliable bike. I know all the touring bikes were redone for 2009. Lots of low mileage 2003-2007s. Thanks again for the help. Didn't forget about the rain gear....working on bike first

 

Use to live in Philly...Rt 30 across Pa until Pittsburgh is a good "historic road" .down 982/119 to unionville then pick up rt 40, pick up 50 outside Kansas city, and take that all the way.. Alot of towns,traffic east on St louis, traffic,flatlands mountains, desert, etc,..It's a basic route to follow been there done it.. you'll enjoy it..

 

Hackd, as an aside you mentioned st joe mizzou and Stetson Hats. Some trivia. John Stetson founded the Stetson Hat company in Phila in the 1860s. My grandmother worked in the Phila factory (shut down in the early 70s) after "graduating" from 6th grade.

Test rode bikes at dealer on Friday Am and liked RK best. Based on advice from this site, checked craigslist on fri night. Found a good deal on a used one, checked it out on Sat and will pick up tomorrow.

Thks to all who commented on east to west routes. The "boss" wants to go South first so she can have dinner in Knoxville with some people. Looks like we will head 30 west to 81 then head to Skyline Drive. Someone mentioned the Dragon to her so now she wants to see that as we head to knoxville. We will likely head thru TN to Memphis and are working the plan from there.

 

Reason I mentioned the Road King is because you now ride a sporty. King like the sporty; except, easier ride and I feel easier handling. The bikes with a front fairing handle different, but having said this, you may want to test ride a dresser one more time. It will provide more long ride protection then the RK and I think your passenger will be happier.

 

Here is the new RK. Did test rides last fri at dealer. Took the advice of several of you on this forum and checked Craigslist on Fri night and the motorcycle gods must have been looking out for me. 2009 RK with 1013 miles was listed on the site. Checked it out Sat and had it delivered on Tuesday. Thanks to everyone for their advice. Planning for the trip continues...

 

We are leaving the 1st of Augest. From SJ to Ca. 3 weeks of wind in my face and whatever. Good luck and rember enjoy the ride!

 

Crash55:
Ride Safe. Did you pick your route?

 

SWEET!! How much, if you don't mind me askin'?