Anyway I'm looking for advice and hints. I've said I'm going to try gaming paper but I think I'll need to pickup pens and other tools. What is recommended?
If I want to draw a bunch of trees, free hand them or does someone create a stencil or stamp for them? Should I get a caligraphy pen or brush for lettering? How much time am I looking at putting in to a map?
You can get a lot of mileage out of a pad of 1 inch grid easel paper, a pack of color pencils, and the old faithful 64 box of Crayolas!
But it depends how artistic you need to be, as well as how many maps you need to make. I've been doing my maps this way for a long time so I got fairly good at doing functional and basically pretty maps, but then I don't get too bogged down with minute detail on them.
There's a thread here somewhere where someone has posted pics of all the WOTC dungeon tiles, and you can take your lead from those as far as trees and stuff, as well as how to shade...which is important with battlemaps that have drops and elevations. (Direct top-down perspective has some interesting challenges with regards to cliff faces and things like that.)
Anyway, bushes are easy - just a group of green circles, each circle shaded darker on one side and lighter somewhere near the center. (those are generally difficult terrain) Trees start with a dark brown or black shape that takes up most of one square - its probably somewhat Y shaped. (That's the trunk, and serves the same as a pillar in a dungeon, in that it gives you cover.) The foliage part of the tree, of course a darker green than your base terrain color, emenates out from that Y. That part can be as big as you want, depending on the tree...usually extending one square further than the trunk, but you can vary it a little. (This part has no effect on characters that have their feet on the ground, but I like to sometimes call it difficult terrain for flying creatures if they're engaged in combat) Again, look at the Dungeon tiles and poster maps that have already been produced and take your cues from those.
And btw I wasn't kidding about the Crayolas. There's a number of decent earth tones in that box. Here's what you do: Get your 64 color box and pick out the ones you'll use for shading big areas. Break those ones in half so you have one end with a point and one without. Take the one without and peel the label off it - that one you'll lay flat on the paper and shade with the side of the crayon. Its infinitely faster that trying to do it with color pencils. (I've played with the idea of using watercolor paints but heven't got around to that yet.)
So say you're doing an outdoor combat in basically generic terrain. (I usually lay it out "small first" on regular 1/4 inch graph paper.) Decide how much space you need, and then mark your terrain lightly in pencil on the graph paper. Use the color pencils to do your details, like rocks, bushes, pools, tree trunks etc. Get that stuff how you want it, then grab your broken crayon and shade the whole thing. As a final step, I like to use a yardstick and go over the gridlines with a fine black or gray marker. It makes it pop, and looks nicer than the blue lines that are on it....but its also easy to screw it up - so be careful, or skip that step completely if you can live with the blue.
As far as calligraphy pens and such, I don't generally have wording on battlemaps so I can't say. Stamps can be pricey, but I could see a use for certain ones IF youre making a new map all the time. I don't bother. (my Mrs is into stamping and has a small fortune invested.) I've made 8 generic grass/tree/bushy terrain tiles, double sided and laminated. They're each the size of a normal piece of paper, but if you put them all together its a little bigger that your standard WOTC battlemap, but I only usually use 4 at a time...that way you can scroll. I've gotten a lot of mileage out of those.
Doing your own battlemaps can be fun, and really helps. To my mind, nothing bogs down the game more than drawing the encounter areas up on the fly or arranging the tiles. I've always done my own dungeons, and realized one day that drawing it out full size on a 1 inch grid didn't take much longer than drawing it out on regular paper - which I was already doing anyway. The next game I just plunked down each room as we went, and was flabbergasted at how much time we saved compared to doing the wet-erase battlemap thing...and it looked a whole lot nicer too.
The beauty of it is, when you're done you can stick them in a folder and have them if the PCs need to go back to that location, or just recycle terrain and dungeon rooms. To this day whenever I need a keep, I pull out the map I drew of Eralion's Keep from Crucible of Freya, one of the very first 3e modules. Once you've made it, its yours. I if you stick with it, sooner or later you'll have a pretty good collection. (Just make sure when you play that you still have the trusty blank battlemat under everything else, because sooner or later some pesky player is going to do something you hadn't prepared for, and you'll need to draw it out anyway.)
One further tip, and this is me respectfully disagreeing with a prior poster: If you can, avoid rolling the maps up. They play better when you're not sticking coke bottles on the corners to keep them flat. (although the plexiglass idea is cool) You can make an oversize poster folder out of a larger piece of cardboard folded in half and stapled or taped on the sides. Storage is a cinch, just stick the folder behind your dresser or bookshelf.
In closing, doing my own battlemaps has sort of become my hobby-within-the-hobby, and its always cool to break out a new map that you made yourself. And believe me, mature players tend to appreciate the effort. Just stick with it. Its like anything else - the first couple might look like a grade schooler's art project, but don't be discouraged - you'll get better. Besides, its D&D, not art class. As long as it functions and is reasonably pleasing to the eye, its all good.