Xamarin have a tough line to walk - larger companies will happily pay that price, while still being reasonable for indie developers.
Xamarin support is excellent - their forums, twitter etc. I haven't worked with a vendor before that has been that helpful. Xamarin need to cover their costs.
I've been using Xamarin Studio for a while now for both iOS & Android and its fine.
It is not that hard, just put a clause in the license that oblige the corporations to buy their related pack
There really should be a one-man shop deep price break. I've used the iOS Pro edition for years since I got grandfathered in for my small iOS app but I don't come anywhere near to breaking even with that so I can't consider adding on Android at full price. I've love to but since I have Pro iOS I can't even add on non-Pro Android licenses either. My little app is a labor of love type of thing with a small, niche user base, not something that will ever cover my costs yet I don't want to give up VS and all that muscle memory and familiarity, etc... I can take a little loss each year for side projects but I can't lose $1800/yr.