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Unfortunately, in recent years I've found myself to be a bit of a perfectionist about my main project, so my image of a map being "good and good forever" will probably cause me to redo stuff that many would view as somewhere between good enough and excellent. You can take this as you will before reading everything else I have to say.

I used to just wing it with my maps, which works if you're looking to give off what I would call an "old 2007" feel, where the layout is basic but reasonable in terms of design and how the player can move through it, but I've found that planning out the structure of your town/dungeon/world map before you start on it works wonders by allowing you to both get a feel for your area and give you a sure-fire way to keep track of your progress if you should need to take a break in the middle of this beast.

Now, if you're any good at planning this should be enough to suit your needs for just about anything, but there may be times where making a full page plan would cause you to pump out an area that's probably every bit of twice as large as it should be. In times like this, going for a plan consisting of smaller, key sections of your map would be your best bet while waiting until later to decide where these places would work best at and what can be placed in the gaps to make the most out of this map.

For the actual construction of the map, namely a town, I've found it better to build housing and major buildings first and the terrain later, as this will allow you all the space you need when it's all said and done. The other way may cause you to be left with an odd sized/shaped chunk of land with absolutely nothing to use it for as it's too small for a building to be placed on it and too big to be left alone. In these situations, not even a collection of trees or a small cliff would help as your town has exposed it's weak point design-wise. Once your buildings are placed, the terrain (cliffs/waterfalls) followed shortly by the trees/rocks/etc should come next. This is where an overall idea for your town would come in handy as you wouldn't have to guess what the shape of your terrain should be to make full use of the smaller details.

Once this is all said and done, I would recommend making small changes and additions for any 'weird' open spot, such as a roadside merchant with only a crate, box, wood platform and his wares to his name. This sort of thing would allow you to make a specialized shop for black market goods or even a financially-troubled fortune teller; this all depends on the mood of your town.

*Continued later*

...Maybe I should follow this process as well.

I'm pretty much addicted to RM2K and RM2K3 over RMXP / RMVX, and since I don't like using rips, I usually try to make do with the RTP. But I often find myself limited by the tilesets in the RTP and it takes some imagination to make stuff look good.

Hero's Realm is probably still my biggest role model in that aspect. Sometimes I look at those maps and think, damn, how did he come up with that?
Max McGee
with sorrow down past the fence
You know, this topic has nothing to do with game theory or game design theory, and it only barely fits into the topic of game design; this is about technique, tips and tricks, not design choices or theoretical musings.

Not sure where I'm going with this (and I know lots of topics, including mine, don't really fit in their respective forums), just a random observation.
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