The phrase “total headache” doesn’t BEGIN to describe how you’ll feel. 
I set out to learn Objective C a few summers ago. I’ve been making standalone software for years using scripting languages (SuperCard and later Revolution/Live Code, and some AppleScript and CLI), and I quite enjoy digging into PHP. However, Objective C gave me migraines and my learning project was an utter failure.
It was in no small part because all the documentation I found assumed certain critical but opaque things to be understood, going from dead-simple “Hello World” projects to ‘WTF?’ in one leap. To my knowledge nothing’s changed: it’s all theoretically learnable, but Oh My God you should plan to do this in some kind of face-to-face learning situation where you can get direct, relevant help as you go.
As for the whole web site vs app thing, they do very different things. I’d say in this kind of case, if the client’s customers find him online and are NOT regular, frequent repeat users who have very specific service customisation needs, an app would be a waste of time and money. Apps are money sinks. Before he goes an inch down that road he should work out exactly what an app would REALLY offer that a web site couldn’t, and determine how much of a difference that would actually make to his bottom line.
k
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