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I have only been on one fly-in but guided for several years back in my younger days (a long time ago)
On my trip I chose house keeping because I wanted the freedom to eat what I wanted when I wanted, the idea of having to be back at a lodge for supper right in the middle of a good bite didn’t appeal to me.
I chose fly-in because I wanted something remote for my son and I, no cell phones, no internet, and no one else around to bother us.
We had 14′ aluminum boats with 9.9 pull start and padded swivel seats (two per boat) which was quite adequate for the lake we were fishing, It was a smaller lake, we didn’t have long runs from our camp to get fishing, and we didn’t have to worry about rough water. A cedar strip boat requires maintenance, an aluminum not so much.
Guides; I think are important especially if you are fishing big water or in something like the French River system where there are numerous hazards. In our case some very basic knowledge and a good map was all that was required.
Repeat or move around; well I have only ever done one fly-in and I won’t be going back there but there are a few reasons for that. In the past though when i have gone on holidays and found a place I really like I tend to go back to where I’m comfortable rather than explore and take a chance.
Hope this helps, good luck!