Been there myself. I started with a gen. I discovered this wonderful community. Sold my gen and stocked myself full of reps.
Next, I picked out all the tells. Started selling them and getting Frankens instead. Obviously, spending $1,500 to $2,000 on Frankens and superfrankens is easy. Don't get me started on the Daytona's. See my MQ Paul Newman dial thread which will set me back +$1,000! All said, I've spent considerably more on all my reps than my original gen!
I'm now considering another gen. Why? Like others have said, a lot is personal. I can afford the odd $3,000-$4,000 gen every now and then. What I cannot afford is the $25,000-$50,000 gens. I've convinced myself (for now) that the modern Rolex such at the above mentioned price points is affordable. Vintage Daytona's, Subs and SDs will have to be Frankens. The 6542, that will also have to be Franken.
My PAMs... All reps for now.
I'm sure you will end up questioning yourself again and again. Back and forth we go.