The bit of strategy you want to leave the weather briefing with is a number: "If I can't fly that route at such and such an altitude (the number) in good VFR conditions, then it is time to land and regroup."
That weather briefing is available from a number of sources, but a pilot planning a VFR flight is well-advised to talk to a briefer at a Flight Service Station. That is not because of better weather information, but because of possible areas of temporary flight restriction along the way. The TFR information is available in other places, but every pilot setting out on a VFR cross-country should play the old cover-your-ass game by asking an FSS briefer specifically about TFRs along the way. The FSS folks can make sense of the gibberish describing a TFR, and this is just something pilots flying VFR should do.
The next step before setting off on a VFR flight is to make a navigational plan. The basics of this plan are the same for a clock, compass and map flight, or a VOR navigational flight, or one with a GPS, which everyone should be using by now. Backstops are the cornerstone of any VFR navigational plan. Just using the oft-violated airspace around Camp David as an example, virtually all the hundreds of pilots who have strayed into that neverland didn't have an adequate plan to avoid the area. With a plan, you miss it; without a good plan you might be in violation. Backstops, in the form of surface features, VOR radials or GPS waypoints can be used to steer clear. For example, staying east of Highway 15 or north of the 270 radial of the Hagerstown VOR, or using airway intersections in a GPS flight plan, can keep a flight clear of Camp David airspace when the area is not expanded because a VIP is there. If the Flight Service Specialist says the area is larger, use backstops that put extra miles between your airplane and the area.
Because this is an election year, TFRs will be in abundance because of campaigning.
Backstops are also useful in dealing with other regulated airspace. If you are headed for, or flying by, an airport covered by Class B or C airspace, identify points over which you will fly to avoid the airspace, or have a location where you will call and establish contact before entering the airspace.
That is all part of the plan.
Fuel is part of the plan, too. The best deal is to always land with an hour's worth of fuel in the tanks. In preflight planning the winds aloft forecasts are used to estimate the groundspeed, which is in turn used to estimate how long the flight will take. The best number to develop in planning is the required groundspeed to make it there with the desired fuel reserve. With that number developed, keeping tabs is a lot easier later on. One other thing: do peer into the tanks to make sure the planned amount of fuel is indeed on board.
Many pilots use only the "direct to" function of a GPS. That's too bad, because the flight plan function can enable precise navigation that avoids TFRs and other regulated airspace and also keeps the airplane away from inhospitable terrain. The GPS units have all the airway intersections and airports in them, and there are enough of these to enable a precise flight plan that keeps the airplane in good air, unfettered by politicians, airliners or rocks. There are times when you can fly long direct legs, but the only way this can be known in advance is by making that plan.
Finally, if you have passengers, while you are planning become familiar with points of interest along the way so you can point them out. I fly to and from Ohio a lot and in doing so pass over Point Pleasant, West Virginia, at the confluence of the Kanawha and Ohio rivers. I always show it to passengers and tell them that my seven times great-grandfather was killed there, in the Battle of Point Pleasant, before the American Revolution. Just after passing Point Pleasant, I fly over Gallipolis, Ohio. I always ask people how they might pronounce that. I didn't know. Then one day a passenger pronounced it Gallo-police. I asked him if he was sure that was correct, to which he replied, "I was born there."