I think comparing self-hosted to self-hosted makes more sense in this case, as comparing self-hosting to managed-hosting can be a bit misleading if you’re only looking at $ price as it doesn’t factor in the cost of your own time and effort in learning and problem solving, etc. Obviously for some that’s a main part of the fun, so doesn’t feel like a cost at all. 
But if being a sysadmin doesn’t appeal and you want something to just ‘work’ (and have a handy and knowledgable person you can email when things don’t) then it’s likely worth the extra money for managed hosting.
I’m in the standard install DO camp for my self-hosted instances. I started knowing nothing and managed to follow that guide (along with some advice on Meta ) and have picked up quite a few things along the way. I’ve found it all really interesting so far and I think doing it this way introduced me to a lot of useful info early on (as @merefield said above) which I think helped a lot.