Sure, if you want/need some "pointy-klicky-UI" for all configuration; cisco is definately the wrong choice. If you are familiar with IOS and the cisco ecosystem, it takes little to no effort to get used to the wireless gear from cisco. Just as with catalyst switches: this stuff is a "fire and forget" solution - configure it and it just works forever and doesn't need occasional waving of a sacrificial rubber chicken over the UI.
I never get why networking gear nowadays needs all those bright, flashy browser UI for configuration where deployment gives you arthritic index fingers and takes orders of magnitudes longer to configure than just uploading your (script-generated!) IOS config template. heck - these things can be even managed via chef/ansible/puppet/etc or your home-brew scripts at huge scales without ever touching them. And If I need monitoring, I just poll devices via SNMP and feed it into my $monitoring-solution, I don't need that functionality on the device itself, especially not as an isolated solution that won't talk to anything else and only gives me a pre-configured subset of informations I can't change. And while ranting: The management interface of those devices shouldn't be even accessible from the network where the people sit that need/want those flashy graphs...
Call me old-fashioned, but I really don't *want* all that flashy browser/app/cloud/smartphone/hipster stuff on networking gear, I prefer a well thought-out and documented CLI and SNMP MIB over *any* UI. Those browser-based UIs drag a metric sh*t-ton of other software along with them, which is drastically increasing the load and attack surface. I'm not petting my switches/APs all day long, every day and want to watch pretty graphs going up and down - I want them to *just work* and if they don't I get informed by my monitoring solution and can look there what really happened - across *all* devices and services, because usually the foult is not the device that just vanished from the network and now even cant' show me it's cute graphs to tell me why it is unhappy...
To get back on track from this little rant (sorry about that
), I completely agree that you sholdn't ever consider meraki - that business model is purely made for beancounters, so avoid it like you'd avoid them...
And regarding access to upgrades: as soon as you have *some* sort of service contract, you get access to essentially all upgrades, even for EOLed gear (although there won't be any updates ofc). Major firmware releases for older devices are usually available for everyone - you just don't get every single minor release and/or variation (e.g. only IP-base for catalyst switches). Since a few years there's usually only a 'universal' firmware and feature packs (what was once called IP-Base, IP services, Enterprise services etc...) are activated via licence.
Yes - licensing and firmware/feature variants have become quite a mess, but usually you only have to deal with that when choosing/buying new gear. And usually you find those arcane and opaque licensing jungles with every vendor - this is not just a cisco specialty...