But I suspect most people who have been flying for a few years and go beyond the local patch, will use some such tool that will cover at least some of these task
Yours and my planning approach is almost identical, bar the different software we use.
Absolutely not. One cannot plan a VFR flight like an IFR flight, at least not in Central Europe.
Well you can plan it for IFR generally, but you just cant execute it liks an IFR flight. I plan IFR (1000’ above nearest obstable, using intersections or VOR’s, not relying on a visual reference to a town or lake at 5 minutes past 6. What I cant do is stick it in a flight plan for CAS and just go fly it – I have to weave around or above and below whatever obstacles require me to do so. Maybe UK isnt “Central Europe” so thats why I am wrong ;-)
Exactly, I was trying to exclude countries like UK and Scandinavia, where VFR and IFR, if flown OCAS, work pretty much the same.
However: IFR (in CAS) flightplanning is about creating in an FPL that’s acceptable to a computer, mostly. VFR flightplanning is about defining a route that can be flown taking into consideration VMC, terrain and airspace structure.
For a fact, most countries don’t allow, say, landmarks to be put into item 15 of VFR flightplans
Most? I only know Germany, whose dfs-ais tool cannot handle identifiers longer than 5 characters. But they don’t disallow landmarks generally, they just advise you insert spaces into landmark names to cut them into 5 character parts
Skyguide usually hates me for inserting intersections into VFR flight plans.
It really has nothing to do with limitations of the filing tools per se. It was just set up this way so that people don’t put Hinzerwaidlingshofen in there.
As always, flightplan filing guidelines are in ENR1.10 of each country’s AIP.
UK also doesn’t allow landmarks as do certainly several others.
UK also doesn’t allow landmarks
You better tell UK PPLs 
They happily file “Upper Warlingham” or “Buckenham” (also disallowed because it is an airfield, especially if you use the ICAO code) as a waypoint name.
How the various electronic tools handle this stuff, I don’t know, because I always used IFR waypoints only. The old human processing facilities (the FBUs – closed a few years ago) would accept anything and anything was good because it created work. I am pretty sure you can still enter anything into AFPEX or EuroFPL for example. I would be amazed if any system implemented a 5-character limit on the length of anything in Box 15.
It’s certainty a lot easier if long flights don’t cross political borders, and I think this is the problem that needs to be worked out to make light aircraft practical in Europe. For a US cross country through complex airspace, crossing through Class B etc, I sit at my PC beforehand and use Foreflight plus on line airport information (Airnav etc) to write a sequential list of notes in Excel, which I print out. Then I use Foreflight to check the weather/TFRs on my iPhone, right up until launch. En route I use Foreflight plus pilotage (looking out the window). I also have paper charts to cover the route but If I have much I the way of problems I land someplace and figure it out. I don’t file flight plans.
For a simple VFR cross country of up to 200 miles one way, through Classes D and E, I do very little preparation: check weather/TFRs on phone, plus plane/fuel, plus a few hand written notes for frequencies to make sure I have them. Depending on the route I might make a magenta line in Foreflight.
How the various electronic tools handle this stuff, I don’t know
RR and Skydemon both do nothing about it. Skydemon at the very least has a remark below the route field of their FPL function saying “use only ICAO route designators”.
It was just set up this way so that people don’t put Hinzerwaidlingshofen in there.
Do you have any reference for that? I was told that this was just an oversight…
As always, flightplan filing guidelines are in ENR1.10 of each country’s AIP.
Obviously. Can you point me to the exact paragraph where the german AIP forbids or even discourages to put place names into VFR flight plans? For NVFR, germany wants essentially IFR plans. And for border crossing, they require you to locate the nearest village on the 1:500000 ICAO chart and put that into the flight plan.
UK also doesn’t allow landmarks as do certainly several others.
Well, the UK is always different. Who else? UK isn’t most countries, for me anyway.
Skyguide FIS will certainly know where the Hallwiler See is, but certainly not where OBEDU is. So they don’t like flight plans with intersections for VFR.
They happily file “Upper Warlingham” or “Buckenham” (also disallowed because it is an airfield, especially if you use the ICAO code) as a waypoint name.
But unless you go out of your way to use SD or EasyVFR etc.., you only have ICAO codes, NDB and VOR references. Hardly any IFR intersections exist on the standard map besides those on zone boundaries.
Conversely, and equally unhelpfully, ATC at least OCAS use references like Upper Warlingham or whatver is local to their specific area, which implies local knowledge. But then life as a PPL without an IR, and for a lot of people there is no strong demand for change. For me, its a PITA not to use IFR waypoints but then I prefer to use the decent tools.
