Yup! The interstate across South Dakota is much more scenic than the interstate across Kansas, as shown in these Google Maps street views. There is no end to the great scenery in SD.
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My basic suggestions would be to make sure that your bike has either new, or at least recent tires and battery.

Prepare a "checklist" well in advance of your trip for the items that you may not be able to purchase on your trip: Meds, eyeglasses, cash, credit cards, D/L, bike registration and insurance, cell phone and charger, and an extra bike key well hidden in your luggage.

A 5,000 mile trip is really no different than 10 500 mile trips.
It's like the old joke: How do you eat an elephant? One bite at a time!

Pace yourself and enjoy the trip. Don't impose mandates on yourself. Find things on a map along the way and take the time to stop and see them. If you have a rainy day, kick back and enjoy it with a magazine and a few beers.
If you do manage to do two-five hundred mile days, reward yourself the following day with a late start and/or a short day and take in some sun by the pool and a few drinks! It's a pleasure ride. ENJOY IT!

 

I think that you can average about 50 mph over 500 miles, taking into account gas and food stops. But to do that, you will have to hit 70 to 80 MPH most of the time. And that can beat up anyone. Open faced helmet will even make it worse. If you stick to the plan, I strongly suggest a full coverage helmet and always wear a leather jacket and pants. In other words, you will have to keep yourself out of the weather.

And those 500 mile days will disappear the first time it rains. The rain will beat you up, as well as the wind.

So, to make those 500 mile days, will end up taking a 12 hour day, because you have to pack in the morning, and unpack in the evening. So, Eat, ride, sleep....

That being said, here is my experience with long days. Something happens around the 9 to 10 hour point. There is a calmness that starts to set upon you ..... almost a mystical transformation where you become one with the road, the weather, the wind, yourself, and your bike. It takes a bit to get to it, but it is truly a wonderful experience.

The five days out will seem much easier, because you will be heading East in the afternoon and evening. So, the sun will be behind you, as will the wind.

Coming back will be much different, because the Sun will be in your face in the afternoon and evening, and that will make you more tired at the end of the day. Also, the wind will seem worse, as you will be riding into it.

Make sure you hydrate like hell and eat constantly. Your energy can drain pretty quick if you are not drinking water.... not coffee .... and not eating which will keep you calorie deficit.

I eat lots of spaghetti when on the road. I find it keeps my energy up. I also eat breakfast, and snack all day on energy bars and sandwiches.

Here is my trick to get the last two hours in. I stop at MacDonald's (because it is quick), eat two cheese burgers (protein, calories and carbs) , two apple pies (sugar hit, calories), two chocolate milk (energy drink) and take a cup of tea to go.

I don't know, maybe after looking at that menu, I am actually hallucinating for the last two hours..... hence the Mystical Transformation....

... But I digress ... what the hell, who are we to argue with a "Bucket List" event....

 

It's a good idea to stretch at each fuel stop. Keeps the blood from clotting in your legs. Seriously. Us older guys need to kinda watch out for that. Buddy of mine had clots form in his legs from driving for days on end. They migrated to his lungs and could have ended up in his heart...which may have killed him, or even worse! (Worse?!?! )

I do a bunch of the stretches I used to do when I was a runner. (That was 15 years and 40 pounds ago!) I'm sure that people look at me and wonder what the heck I'm doing, but I don't give a hoot. I do stretches #2, 3, 4, 5, and 7. While on the bike I'll put my legs on the highway pegs and straighten them out and bend myself forward so my face is near the bottom of the windshield. Really stretches the ham strings and glutes (butt muscles.)

 

Crossing this country on a motorcycle is the highest and best use of a bike. Chattanooga is my favorite southern city. The view and history is great. Lookout Mountain and the battlefield park is a must.

I'm 76 and still crank out 7 to 9 hundred mile days. Just got back from Vegas with three days there and three riding days back averaging 700 miles per day.

Go 120 to 150 miles fill up with gas, empty your tank, hydrate and walk around a little bit. Repeat that from 7am to 7pm and you can cross this county with ease. It is not any more complicated than that.

Catch all the states via interstate routes then when you do that begin to explore each one with local roads. Both those experiences are worthwhile and different.

Middle America is full of the working folks that built this country. Explore the roads like US 281(American Legion Memorial Highway) from the Canadian border to the Mexican border and talk to folks at the gas stations, restaurants and motels. Great people.

The posters that say the midwest is boring are ignorant inexperienced at touring. Nebraska boring? Go down from Rapid City on 85 and turn at Alliance on route 2 east through the "Sandhills Journey" which Charles Kuralt said was on of the 10 best scenic routes in the US.

I ride ocean to ocean, Key West to the Arctic Circle, 49 states and most of Canada. I have carved up most of the States in the midwest by several routes N and S and several routes E and W. with with over 200K in just the last seven years. Never found a boring thing anywhere. But then that requires what the Comedian Gallagher said was "Eyes that See".

 

My advice is reflected in my logo. Be patient, and wait for a time when you can make that trip in a leisurely fashion, on the backroads (2 for instance). Our machines with their maneuverability are at a wonderful advantage on the back roads. They are at a terrible disadvantage on the interstate. Spend your 15 days on the wonderful roads of Washington and Cali, or ship your bike to Chatt and ride the Smokies, you will find no better riding anywhere (well, maybe include some Arizona / Utah / Montana). Avoid the Midwest, there are just better places to spend your time. Nebraska Kansas Oklahoma Texas Iowa just aint much fun after what the OP is accustomed to on the West Coast, and you are crossing this country way too fast to really Enjoy what the "Eyes [can] See" or the soul can experience if you are making 500 miles a day. You are just beating yourself up, to prove .... What? That you are an "Iron ***"? What is that worth after you are in the grave? The OP is not talking about crossing Nebraska on 2. Probably I-80 and 29.To meet and enjoy the "... working folks that built this country" you have to pause long enough to hear their songs and stories. And Yes, there are a few things worth seeing in Nebraska or in the Big Bend or Hill Country of Texas, but a man's days are limited. Would you rather the Sand Hills of Nebraska or Bear Tooth Scenic Montana, PCH, Tioga, Cheroholla, almost Ad Infinitum ? You have maybe 80 years of active life, you have to make choices where and how you will spend them. I just don't think the gain would be worth the pain as the OP has originally described the trip.


Finally (we all hope) it is not "... as simple as that". the Devil is in the details, and you have to be ready for them. Bad weather, fully booked motels, flat tires, faulty voltage regulators, on and on, all of Murphy's corollaries. If you don't allow time for them, they will undoubtedly get you, "... at the worst possible time".

 

If you do it... the stretch idea. I support doing this every hour. Not just at fuel stops. My king will do a few hours on a tank. Not long stops but get off, stretch, get some blood moving in your legs and lower back. You can do this stopping only for a couple of minutes. Once you start hurting or getting stiff and sore....

try some warm up trips before your actual run. get in shape for it.

Also remember on the istates, big city traffic can kill your progress for an hour or so

 

500 mile days is a piece of cake if you're comfortable on your bike. Just do it. That''s maybe a little over two full tanks of gas depending on what you're riding.

 

I hope that my post above (#11) about SD and KS interstates wasn't taken seriously.... I was being sarcastic, which isn't always obvious without voice inflections. Anyway, I agree with you about "Fly Over Country." I have lived in Nebraska and Kansas all my life. Yeah, there are boring roads, but you can find flat, straight mind-numbing roads in any state. If a person gets off the slab and explores the GON2L (Good Old Numbered 2 Lanes) they'll find all sorts of interesting roads in the Plains states.
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Ok. This might be the best advice I've gotten so far. There a lot of this that rings very true for me. Especially the line

"You are just beating yourself up, to prove .... What? That you are an "Iron ***"? What is that worth after you are in the grave?"

I've done 500+ miles a day plenty of times and I know from experience that it beats me up pretty good. Never 5 days in a row. I am at that stage in life where I feel like I want to get out and do these things I've always dreamed about. But I have to stop and ask myself .... Do I wanna do it just to check a box on a list? Or do I wanna do it and do it right and enjoy it. Easy question easy answer. I'm too old to try and prove anything to anyone.

So ... Maybe I do want to re think my time frame and see if I can stretch it out a little longer. Since I'm still working and am a few years away from retiring, it's hard to take more than a couple of weeks off at a time. Three was stretching it.

Thanks for all the help and advice. I like coming on here and throwing around ideas. I don't have anyone around that I can do that with so the next best thing is my internet friends