No idea what you mean by this. Most major free apps are free on both, and plenty of the "free" Android apps are junk/spyware/malware, or you'll have to sort through a bunch of different ones to get the features you want, and entirely possible you won't find one or you'll end up paying to get it just like on iPhone. Plus, even Google's own apps are often superior on iOS, and I'll let you guess what that means for 3rd party apps. Its not as bad these days (and there are a few that the Android app is better, although I can't think of any off the top of my head), and sure there's issues with default app situation on iOS, but its not like Android doesn't have plenty of its own issues. Performance is still better on iPhone (haven't noticed "we totally super duper absolutely fixed performance and made things smooth for real now" claims for the newest Android, which means we'll be hearing it next year after things bog down yet again). And let's not forget the mess that is updates (in fairness, Apples has had issues with updates causing problems, but you typically at least get the update and don't have to wait months to find out if you actually do or not; my ATT LG V10 still hasn't gotten a main Android update and I can't force one).
For me, its a tossup, and I'm not sure I'd give up years of built up apps (guarantee that if you've spent much money on iOS apps you're not gonna get equal features for free on Android) just over drag and drop. Which pretty sure there are programs that let you wirelessly drag and drop and plenty of apps can be aware of and use the files. In fact VLC itself integrates something like that:
https://www.videolan.org/vlc/download-ios.html
With regards to the headphone jack, new iPhones still come with the dongle, don't they? So you don't have to use wireless headphones. And talking about quality, lots of Android phones either don't come with their own (gotta love carriers literally removing them from boxes just because...) or they're no better than Apple's (you do know you don't have to use the official Apple ones on iPhone, right?), so that shouldn't even be weighted as a knock against iPhones (especially since several Android devices are doing the same thing). And the inline DAC/mic devices are more likely to be tailored to iOS. Actually general connectivity (connecting to external devices) is better with iPhone, isn't it? Aside from USB to PC.
I don't know exactly what the OP has spent a lot of money on with iPhones (the phones themselves and accessories, apps too?), but you'll end up doing that on Android too. And I guarantee you'll encounter plenty of minor annoyances that will bug you just like iPhone (some might be device specific, but . That's not to say you might find it less annoying than iOS (seems like a fair amount of people do), but at minimum you'll be spending a lot of time tweaking things. Oh and stuff like ApplePay exist on Android, so not really getting how you think you'll be getting away from that (I don't recall Apple being obtrusive and popping up forcing you to use ApplePay?). Speaking of pop-ups, I love how I have to do a special thing to get ATT's stupid AddressBook from popping up every single time I click Contacts using the built in phone dialer/contact app (and sorry but finding another one was a nightmare that ultimately proved pointless since they all had their own issues).
Don't get me wrong, there are some great Android devices, I just don't think the overall situation is any better than iPhone (and I'm not an Apple/iPhone fanboy either, I agree with many criticisms about it, I just don't get the way people act like Android doesn't have just as many issues; my main point of contention was Apple not using AMOLED and the cost of storage both of which are being addressed). I'd guess that plenty of the things that bug you on iPhone actually have workarounds too (see VLC, do you have some aversion to using wi-fi, or did you just not know about that ability?).
I suppose it comes down to viewpoint. Some see Android tweaking as a positive, I see it as neutral as its often either required (FYI, file management probably won't work just as well as you're used to on PC; also have fun, as just search on here for the people that were using some popular file management app, where the app maker decided to push people to pay for it by removing features and making the non-pay one an ad-infested data mining nightmare, think there were other issues with it too) or you still can't tweak it to get what you want (but you'll spend plenty of time trying to, and there's less safeguards when it comes to malicious software). And let's not forget software bloat. And if you're someone that isn't very tech/software savvy you might actually find Android to be worse.
Not trying to completely discourage you, just know what you're in for. Hopefully if you do switch you won't have serious problems and it'll go well. I personally would strongly recommend you buy a decent lower end device (Moto G?) or older flagship and try it out before seriously trying to make the switch. That goes double for your wife, since in my experience that is asking for trouble.