21 vs. 23 inch, To rake or not to rake!!

Okay, so I'm at the point of putting some serious money into my bike and I can't decide if I want to go with a 21" wheel or rake have a reputable builder cut and rake the frame and go with a 23". It is obviously more expensive to rake it but I'd rather only do this once.

As of now I plan to do extended bags and do the rear fender but I'm still unsure about doing the longer stretched bags and fender. Obviously I have a budget and I'm trying to keep this within a certain amount but certain things are better done together. I guess it comes down to a few choices.

1. Keep the front end stock and go with a 21" rim with normal extended bags.
2. Rake the front and go with a 23" rim with normal extended bags and a rear fender.
3. Rake the front and go with a 23" rim with longer extended bags and a rear fender.

Obviously, Number #3 would be what I want to do but the cost along with the other things I'm doing is going to put me over budget. Who has been here and what did you do? I only want to do a lot of this once and would rather not change the fender/bags or front rim in a year or two. Do those of you with 21" rims wish you went bigger? Do those of you with 23" in rims have any regrets.... and no, not meaning wishing you went with a 26" inch rim LOL.

HELP