At night? I can't even get to the BF until 7 or 8pm and then he has to drop off our luggage and his dog, and my dog I can't drop off after 8pm, then we get to the airport around 9 or 10pm, off by 11pm, there by 4am? And wake everyone up? I don't even think they have the place reserved until Friday and I go to bed by midnight each night. I'm not flying at 2 in the morning. Plus I can't check in with the FBO and we don't have a car.....
Heh. I told ya Logistics was half the battle using light aircraft to travel.
A lot of us have had to "train the boss", and sometimes you can't. But it's worth trying to teach them.
Bosses that don't understand passions for living and can't be a tiny bit flexible are usually pretty sad people. I hope for your sake you can find a better person to make wealthy.
You're enabling his dreams, he could at least be understanding as long as you make up the time. Anyway...
As far as weather goes, is there a meteorology course at a local college? I have found the multiple met courses I took long ago to have been invaluable in looking at weather.
And weather still falls under that, "It is what it is..." category in the real world.
Forecasts are great but they're still just an educated guess.
I've done VFR XCs where the plan was to go to a halfway point where the WX should be good and treat the second half as a possible "cancel and air return" to the starting point.
As long as you always have a true "out" you can always turn around and go home or where ever you came from.
Regarding the Bravo clearances... Flight Following and saying you're VFR to [destination] helps. Controllers tend to help those of us going somewhere just a tiny bit more than just "VFR" wandering around their airspace.
They may give you vectors or "Direct To" routines to keep you out of their congested areas, but it's fairly rare they'll turn you down outright on a VFR XC.
Once one controller puts you in the computer with a destination you become just another target being handed from controller to controller, very efficiently.
You're not 100% "in the system" as a VFR pilot but once you're datablocked and tagged up, they mostly just treat you like you are.
Jesse's comment that you are over thinking is true, but we all do it at first. These days I look for a "window"... weather comes in big waves, naturally. If a big wave of crud is "crashing ashore" from the Pacific, you're driving. If your flights can be between he waves, you're good. The rest would just be an exercise in judgement along the way.
Launched out of Denver once for Houston, thunderstorms popped along a line from about College Station, TX to Houston that afternoon. We ended up continually diverting to the right and out into West Texas knowing the line would move East and no lime forming behind it (via eyeball observation). Arrived KDWH at 22:00 local time that night. Waited out the line on the ground at an airport way off our planned route. Found a good Chinese place to eat at.
Weather turns VFR XC flight into unplanned adventures as long as you always turn toward your "out".
I look harder for what my "out" is going to be than the route weather if the weather is up for grabs. "Where is the place I will go if this turns to crap?" I can look out the window at the weather on the route. I need to know where to go to make it look a whole lot better if the route looks crummy.
"End-runs" around stationary weather patterns are a common tactic. Thus... all that pre-planning may be for naught if you're really trying to get somewhere. I didn't have a course line plotted for that run around the thunderstorm line, but I did know better weather was there and how much flight time I had in my tanks. A quick calculation of groundspeed and a look at the chart for a "big enough" airport to probably have some services, and some VOR twiddling, and we were landing 200 miles off course at a cool little place to go inside, pull up the radar map, and wait it out.
That's pretty much how real VFR travel gets done, IMHO.
Don't disregard 1-800-WX-BRIEF. They'll give an "Outlook Briefing" anytime for looking forward for the trip home and in rapidly changing conditions you can land, look at weather maps at most FBOs in the pilot lounge and call them again for updates.
Plus you need to close out that last VFR flight plan and open a new one anyway, right?