Description for Dragon and UOL features (Punt map tool was not used by me, so i'm have nothing to judge obout it):
DRAGON
Advantages: Dragon is minimal option to make your map very quickly. Consisting only two programs, handful and easy-to-understand scripts, pack of issues for Photoshop to work with your map. Shortly, dragon is Very easy to be customized for your own needs.
Disadvantages: Dragon working only with indexed color bmp's which ones have only 256 color palette, so there may be 256 tile-altitude slots for one map. Sometimes it can make bugs, so there better to backup your map after each test rendering.
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UOL ( UO Landscaper )
Advantages: UOL is working from two 16bit bmp's, one for altitude, one for landtiles. It making possible to make maps from huge amount of tile types, with huge difference of altitude, so the result is ideally made map.
Disadvantages: UOL is a complex of programs and it needs some time to understand clearly how it works and less handful. Scripts is barely untitled and there is no base to understand how they works. Unfriendly for custom graphics, cannot paint auto-statics (rocks, trees, other items that will be placed in equal land type) to custom hue.
To make new gumps for paperdoll, you first need to draw them, of course
then you must get Mulpatcher tool which is very similar and can be finded in some places (try search). Some tutorials may be finded on runuo.com. I'm sorry that i havent them by myself, i'll thy to find them myself, but im not sure, so i recomendate you to look for it there yourself. Sorry if i was not useful enough for you.