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Yes, I would start with simple cotton diapers like flats and covers!

I personally wouldn't... sometimes I wish I never started CDing...

About the leg rash - L often gets a rash around her leg from the CD rubbing her, so that might not even solve your problem! That's the only rash she gets - no actual diaper rash, but her poor thigh...

CD can be expensive so I would probably only start at that point if I was fairly certain that I was planning on another baby that would also use them. Have you tried other types of diapers or putting some cream with dimethicone where he gets the rash? Kind of like the idea of that stuff you can put on your thighs if they rub together so you don't get a rash?

Perhaps you could try a hybrid diaper like gDiapers? You could use the washable outer cover and the disposable insert. Are there any cloth diapering stores in your area where you could rent diapers for a bit to see what you liked or if it got rid of the rash?

I started with a hybrid system of Gro-Via. You can buy liners that you just snap in and then reuse the shell. Flips are the same type of thing but the inserts don't snap in.

I would agree though that a leg rash/irritation probably won't be fixed by CD.

I only would if I knew I'd be having another baby to use the diapers with. Otherwise, its an awfully expensive experiment.

If you want to try, I would recommend a pocket or similar style that has the fleece lining over the leg elastic. We stasrted out using primarily flips, but use primarily BG4.0s now because especially in the summer, the more exposed (and more likely to be damp) leg elastic of an insert-cover system was irritating my kids legs like you described. You could always buy like 3 that would get you through a chunk of the day to try it, and it wouldn't be that expensive, and should give you an idea of if it will help. I'd recommend buying new over used, since your lo already has some irritation issues, you don't want to compound that with someone else's potential residues, etc.

My friend's son was having major issues with diaper rashes and found that Seventh Generation diapers helped get rid of them. I would try a trial service before deciding to invest in cloth diapers as well.

Also, is it more of a chafing issue than a rash? DD also has a bad rash around the leg holes, but it usually only happens when the weather is super cold and dry. I bumped her up a diaper size and i'm going to see if that helps.

@MamaJ: I think there are a few stores that do online trials!

If you're planning on having more kids then yes, otherwise I'm not sure. I would consider cotton diapers (not microfiber); they seem to be better in the heat for my kids and certainly it will be nice to line dry the diapers. A dozen prefolds and a couple covers won't cost too much.