Disarray - I understand your issue. I am a road warrior 150+ flights per year traveling both in the US, Europe and India.
Since I am on the road all the time I typically don't skimp on the amount of clothes I bring.
I personally have always wondered how people pack in the standard vertical roll aboards. When I have tried everything comes out a mess.
I agree with the other posters, 5 suits is a lot. Even when I go to India for 2 weeks, I only go with 3 suits + sport jacket + dress pants.
I only use garment bags now. My suits never need to be pressed when the come out. My shirts typically come out well and if they do need a touch up, I place them in the shower with is as hot (steam) for a few mins.
After a few years of doing this I have 2 brands I like - Briggs and Riley and Desley.
Briggs and Riley is expensive but their lifetime warranty is fantastic. I have these 2 bags. One I use for 3+ overnights and the other for less than 3 nights in carry on. If I ever need more space than the check in garment bag, I use a small upright which I put all my casual stuff in so my suit bag is not over stuffed which leads to wrinkling.
http://www.briggs-riley.com/category...rment-Bag_U176
http://www.briggs-riley.com/category...174&sec=travel
http://www.briggs-riley.com/simple-a...time-warranty/
The Desley has a warranty but not as good, but is cheaper. So trade off.
http://www.kohls.com/product/prd-128...CID=shopping15
If you are going to be a road warrior I would got with Briggs. If you are only traveling once a month the Desley should be fine.
I have noticed this bag and people say its great. The obvious advantage is the 4 wheels so easier to roll. Less stress on the arm.
http://www.ebags.com/product/samsoni...ent-bag/251121
The brand many pilots use is TravelPro.
Hope that helps.