Sorry this is rambling. Just thoughts on travel
When I was a kid we flew our Piper Pacer to Oshkosh , Florida and Texas a few times from PA. Family of four with all camping gear for a week. OSH is easy camping but tent and gear anyway. Pacer is 100 lb baggage plus cabin stuffing around us. As we got bigger we switched over to the Stinson Gullwing. Still traveling self contained. Then someone would follow with a truck and extra gear. My wife and I started taking ourselves in a Stinson 108, Then Tripacer. Two airplanes and one truck. Then two airplanes became a Queen air. Later after we had kids we've gone with Two Gullwings hauling 10 people and one full truck of gear.
Last year we were back at Oshkosh with our two kids in the same Piper Pacer I flew to OSH in when I was a kid. Full circle except I was in the left seat.
Most of these trips were all low and at LSA speeds. No problem. Just fly until the sky looks ugly. Land and wait it out. Navigation is easy. Just fly point to point on the map, monitor GPS map and keep major turns or destination in the GPS. Never bothered to enter a flight plan in the GPS. It's a wonderful gadget.
If it's a long trip the weather will never be fine the whole trip. Can you time it to spend the night somewhere while the bad weather passes over. Going west it's pretty quick to pass over. Going east you may come in a position with a warm front ahead moving slow that just won't get out of the way for days.
I've flown VFR from PA to California without a problem. All over the US including AK. A VFR LSA is fine. IFR can be easier but it takes more restraint to be able to determine when not to go.
What you take along can vary depending on how creative you are with packing. I'd suggest a good look at the REI catalog and other backpacking outfitters. It makes a big difference if you are camping at locations or staying in motels.
Plan to arrive each night before closing time. It stinks to get to a deserted airport. I've spent the night under and in airplanes many times. In Oklahoma there are blue laws or something so if you travel on sunday nothing seemed to be open. After dark plan on using a tower controlled airport to be able to get to a hotel unless there is something you know to be within walking distance.
The time of year changes things also. If you tie out for the night in winter the frost might not get off the airplane until noon. An airplane with darker wing colors sheds the frost better. Nightly hangars are hit and miss.
WAC charts don't really have good enough detail for LSA trips.
I use 100LL.com a lot for comparing fuel prices in the area I am going. It's similar to the airnav comparison but a broader distance. I print out an airnav field directory when I go to any tower controlled airport. It's big and easy to read.
Look over the planned route. Be flexible based on weather and terrain. Modify the route to keep near areas with airports. Especially if the weather is low. If you can plan to follow an interstate highway thats great. Natural landmarks like rivers are good too.
An ipod helps the time go by. Good headsets. Fix the seat padding. Clean up the cockpit by removing all unneeded wires and junk. A simple organized approach really helps.
Airspace is pretty easy to avoid. Study the charts and look at the altitudes needed. If you have the signoffs then I would use flight following. Most of the time I don't if I'm low altitude below 2000 AGL I just listen to the AWOS/ATIS to update my altimeter as I near airports and make a position report as I pass by. Monitoring the unicom and tower frequencies of whatever facility is closest. Low stress low and slow flying. Altitude depends on terrain, weather and available off airport landing sites. And my mood that day. Usually there is little traffic at that altitude and they are low and slow like me.
Frequently I fly cross country too low for good radar coverage and we have more than one airplane in a group so we are talking to each other on 122.75
Traveling in a group of airplanes has some other rules. The lead airplane navigates, Others follow and monitor navigation. If everyone navigates it's a mess. Pick the same waypoints and compare distances/altitudes if you lose sight of each other. Keep enough distance so your transponders don't alarm the controllers or if in contact use a flight of two. Everyone pick who to follow based on speeds and keep that in mind. There is a lot more to it but that's a start. The previous posts have a lot of good ideas also. We've successfully traveled from PA to OSH in a gaggle consisting of a 172, Navion and two Stinsons. It wasn't pretty at times but it worked.
Try a couple small trips to destinations first.
http://pilotgetaways.com/s is a magazine that has good trip ideas. The $100 hamburger book might also be available.
Using an airplane for fixed date business travel is a recipe for disaster. Drive or use the airlines if you HAVE to be there or HAVE to be home on an exact date. The dates get more vague the farther you travel.
Getting weathered in is 1/2 the fun. Sometimes it's the best stops of the trip. After a while you will pick out stops across the country that are good. Then work them into the flight plan when you travel that way. Could be cheap fuel, good hotel, nice FBO or great tasting pie. Whatever makes it a good stop.
(Guess I'll have to buy a Martin Backpacker.)
