or is it more about the air traffic ?
heavy commercial volume vs. a bit of rain ??
Visual Flight Rules on a nice day... but it looks iffy at the destination !

No it should be where you intend to be when you land

It really depends on if you are planning on filing a VFR or an IFR flicht plan.

I'd always check to see how wet the conditions will be and then I'd make it my business to know just how much ''traffic'' there really was.

Its more about the safety for me....x

Weather is always your primary concern if you are traveling by air and filing a flight plan.

Weather, route ( l like most direct, & avoiding special use airspace.) & wind. -- that is the priority.

l used to flight instruct in Minnesota, & often people from my area would travel ''over'' Chicago enroute to Ohio or other points east. ATC is reaction to how flight plans were filed became very predictable.

If u want to try a nice experiment, file ur flight plan direct so it goes straight through class B airspace (Be IFR or on flight following.)

ATC will then route u FAR outside their class B airspace.

On the return, file from ur origin, to a waypoint just outside class B airspace, then to ur destination.

You will then almost certainly get exactly what u ask for.

That is the difference on how the people who know what they're doing r treated vs, those who do not know what they're doing.

To 'Plan' the flight first consideration is fuel and payload. If that works you check route, weather and alternates. Yes avoid congestion if possible.