All great questions, not dumb at all, Cyrus.
1. Unusual to go 600nm VFR? Not that I'm aware of. Weather planning starts with the 'big picture', the area forecasts, the prog charts...looking at weather systems involving many states. You then drill down for the route of flight and what's going on locally. In my case, there was high pressure dominating the entire eastern half of the country, making the weather planning a very quick exercise indeed, at least for the first leg. The second leg (400nm) had a bit of weather in the middle, and possibly some weather on the end, depending on how quick the front just SW of KADF moved along. It was forecast to start affecting KADF about an hour after my arrival time, but that's not much margin for error, so I filed and few IFR, knowing that GPS direct was a very real possibility and the effect on my flight time would be very close to zero.
Contrast that with coming out of the NY area where the IFR routing can add some delays due to more complex routing.
Had I seen anything odd in terms of weather, I would've given Flight Watch a call to get updated weather. As you can see from the time lapse, it was all very benign.
2. A huge misconception of flying IFR is that you no longer have to look for traffic. Any time you fly in VMC, regardless of whether you're operating on an IFR or VFR flight, you need to look for other VFR aircraft. In Class E airspace, where 99.9% of the flight took place, ATC separates IFR from IFR aircraft only. I did have flight following the entire way, which, practically speaking, gave me just about the same level of attention as I would've gotten if I was IFR in VMC.
Case in point, I have been on an IFR flight plan in VMC and have NOT been told about a plane that passed relatively closely to me (somewhere between 500 and 1000 directly below, a fast moving jet), because of controller workload. Compare that with the flight I just did, VFR, where ATC told me about another VFR aircraft 12 miles away on a converging course, and then gave me 6 more updates as time went on.
When flying VFR, you should be looking outside and occasionally checking your instruments. Checking fuel levels, oil pressure, oil temps and cylinder head temps is something I do throughout the flight, but primarily it's about looking outside (or should be). I won't lie, you can easily get lulled into bad habits with flight following and high altitude flight if the controller is silent for 10 minutes at a time. If they're not seeing anything or talking to anyone, and they're not busy doing other things, then the reality is there's probably nobody out there.
The length of the flight doesn't have any significant bearing on whether I'll go IFR or VFR.
Flying VFR actually frees you up to worry less about your exact altitude and route and actually gives you more time to look outside. Had I been IFR, a deviation of more than 200ft could result in a pilot deviation....that's not true for VFR.
3. Victor airways make up the enroute structure and used to be a critical part of IFR flying prior to the advent of satellite-based RNAV. That said, they're not needed for VFR flying at all. I pay no attention to Victor airways when flying VFR. I do utilize VOR's during the flight if they're available. I make sure I'm receiving them and that I know where I am if the GPS keels over. If the GPS does keel over, I'll then swap to ded reckoning, pilotage (assuming I have visual contact with the ground) or I might consider going VOR to VOR.
Going VOR to VOR from the outset doesn't buy me much. Better to be prepared to revert to VOR to VOR rather than plan for it from the outset.
On leg #1 on the return trip (KADF-3M7), I had an absolute blast using pilotage at 7500ft to keep a high level of situational awareness, even though I was flying within 0.01nm of the GPS direct course. Great way to stay engaged in the flight, and if the GPS keeled over, I would've said, "hmm...that's interesting" and kept going

What's need about pilotage from high altitude is that you can use landmarks 10nm+ on either side of you to verify your location...you don't actually have to fly directly over them.