There’s definitely some planes that are worth it. Cirrus, C172 (Classic), 787, and others.
The airports, eh. Unless you really want one or more of them. I don’t think I’ve used any of them for flying too. I think I’ve found a couple useful assets from them I use in my sceneries.
Totally agree on the delete it all and reinstall first. But, if he really wants the upgrade, then go for it. In a year he’ll never know he had that money. I spend as much at times on dinner for two… sigh.
Horses for courses I suppose.
Just a personal thing but I tend to be now very very picky with Aircraft (having had the sim since launch and having bought a lot of AC) and just tend to stick with very high fidelity addons. Not saying that I’m a great simmer at all but I love the learning experience that a very realistic addon gives. The more realistic the better. As you say the Classic 172 is quite good but with so many AC to fly I am hoping for an even better one from A2A maybe in the future. At the moment, I have quite a few really very good 3rd party AC but never enough time to sim in them let alone any default AC.
As you say, if he wants to upgrade (and it seems he does) then fair enough. It doesn’t really make a great deal of sense to me but then again it doesn’t have to. It only has to make sense to him and I honestly have no problem with that. I hope he enjoys the upgrade 
For personal reasons I dislike the Steam platform and only use it if they have managed an exclusive right to a product I really want, but that is beside the point.
The premium deluxe is still relatively good value, you get the Cirrus, the Longitude, the Baron that allows the BS Steam Gauge addon, the Steam 172 that takes the WBSim addon, the Pipistrelle Virus that is something of a hidden gem and the 787 since the update is now pretty respectable.
Adding it to Steam you would need to buy both the Premium and the Deluxe packs separately.
Switching to the WIndows version you get to keep all your community addons but lose access to any marketplace purchases bought through Steam. This is perfectly normal. If you buy DLC for a Steam game and then buy an alternative version your Steam DLC does not transfer. In very rare cases the developer, if provided with proof of a marketplace purchase, MIGHT give you access to the non-marketplace version but do not count on it, they are not obliged to do this.
not really. both steam and MS Store have the same in-game marketplace purchases, so you can buy the premium deluxe bundle on steam as well.
Won’t transfer to MS Store version though.
True you could just repurchase another full Steam version (edit) but that would still not keep all your marketplace purchases as far as I know.
However I suspect he/she is trying to switch to the Windows version to bypass any potential lurking issues with the old Steam install.
They are both ‘windows versions’. MS Store or Steam, they both only install the MSFS installer. The rest of the sim is installed from there. Literally no difference between the two installer wise.
MS Store version encrypts more, and makes the folder structure more locked down/less convenient though.
Yes they do seem to install by default in different locations, but if you have any sense you change that.
So would a purchase of a second Steam version retain your marketplace purchases ?
I don’t think you’d be able to purchase two on the same Steam account. At least with other games you can’t.
Also, if you were able to, I do not think it would retain Market purchases. This is based on MS saying that if you purchase to your xbox account and then get a Steam version of the game, they will not transfer.
Don’t think you can, at least not on the same account.
Even if you could, you’d get the message ‘this steam account is already bound to a copy of MSFS’ (or something to that effect).
Also, why would you? you already own the game on steam?
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