Looks like I'm not the only one then. As I think about it, I'm realizing all the issues I am having in my map are because I grey-boxed and planned ahead. 

Sometimes planning ahead is impossible, when working in a situation you're not familiar yet. Maybe after, planning ahead becomes more effective. 

To be clear, there are certain global end goals that I do define beforehand, but the way to achieve them remains purposefully improvisational. This is how I work as an artist, in music as well, as I have found with experience that it allows my creativity to take me to unexpected places. I never made anything good with a very defined plan. 

theres a vine texture in AD that I want to use in my map. and I also want to try transparency with brushes, like in sock's metal monstrocity. How do I achieve this? 

Set the brush as a func_illusionary. This allows players/monsters to walk through the brush. You can use the flag "alpha" to set transparency. Honestly, just open up the metmon map and check it out yourself! :) all the authors .maps are included with AD. 

I haven't completely greyboxed a map either...but I have a significant visual plan in my mind of how the layout will be. Ultimately I go room by room and wing it to achieve said layout. It almost always deviates from the original. ;) 

Vines in AD are a combination of a texture with palette colour 255 and func_illusionary. They do not use brushes with the alpha key set to achieve that.

Engine support can be a bit of a hangup - mostly DarkPlaces, since the first download offered on the site is from 2014 or so and doesn't have support. Other modern engines and newer versions of DP support transparent textures just fine though. 

I mention "alpha" in conjunction with "func_illusionary" because he asked about transparency, not because I think its required for func_illusionary to work.

I typed my initial response while still in bed. I should've spaced out both ideas. 

The alpha value will not have the desired effect - the entire brush will be transparent. The vines in AD are entirely non-transparent, but the rest of their texture is. That's completely separate from the alpha value of the brush. 

In an editor the textures will look something like this: https://encrypted-tbn2.gstatic.com/images?q=tbn:ANd9GcS1LSsZWB4Oc0pSm2QDhsSz0fQmW_B5cYNCIy8IXZq4D_0yXWajB9_ySaPj 

The vine feature is called "fence textures" or "alpha-mask textures".. the texture name also needs to start with a "{" character.

(sidenote: it's possible to make them work in the 2014 build of DarkPlaces, AD does this by supplying .tga files. There is a "fixtrans" command in DP that helps prepare the .tga's) 

Most of the techniques I employ are derived directly from "top tier" maps.

Func_illusionary + alpha is in use in ad_necrokeep to good effect.

http://imgur.com/a/2S7ZP 

sidenote: it's possible to make them work in the 2014 build of DarkPlaces, AD does this by supplying .tga files. There is a "fixtrans" command in DP that helps prepare the .tga's
I didn't know that. The September 2016 and newer builds, however, do support alpha-masked textures from the get-go and don't need this command.

@Pritchard The DP site at icculus doesn't seem to be maintained these days. The new builds are not in the /download subfolder but in /files (which is, of course, not accessible via the on-screen menus). 

i have 15 water brushes. there aren't gaps or intersections between brushes.
i tested the map in quakespasm and i can swim without problem of any kind.
can i expect problems or bugs with what i did?
weird bugs, problem with other engines, something like that.

http://imgur.com/a/cqDlp

(i put this message in the QUMP thread, but here is better. i can't erase the other message) 

i'm having problems compiling a map, i have everything set in a profile but i keep getting a error "execution of command 'C:(the path of the .bsp compiler)" andt1.bsp' failed (error 267: the directory name is invalid.)" what do i do??? 

Make sure all your directories have names without spaces. 

none of them have spaces :p 

also, when i try to launch it, this "W_LoadWadFile:couldn't load gfx.wad" appears, the engine is Quakespasm 

I assume you are compiling in Trenchbroom. I am willing to bet you have a small typo or hard to find syntax error in the setup. I am pretty experienced and that interface is too much for my tiny brain. I would suggest downloading and using Necros' compiling utility. Just keep it running and pointed to your map and alt-tab to it when you save. It works beautifully and is very easy to use. After you have it setup all you will have to change is the mapname when you Save As... or start a new map. Download it here: https://www.quaddicted.com/files/tools/ne_q1spCompilingGui103.zip 

i don't know what i'm doing wrong. it seems like i've set up everything correctly, it even compiles(it seems), but the .bsp file doesn't appear in the output folder(and in any other folder). 

http://imgur.com/a/l5klI

uuuuuh...dumb question of the day..why are surfaces multicolored? 

Solved thanks to scampie via twitter.

My .lit file wasnt updated 

i post my config:
http://imgur.com/a/0vqvZ 

@Ranhcase
Did your map used to compile? or are you trying to compile it for the first time?
If is did compile, perhaps try deleting some of the more recently added brushes (save a new version first!), particularly any that overlap.
I've had a similair problem where the map wont compile, and each time it was due to a single brush that must have overlapped in a strange way. 

this message is caused by the working directory.
launch the game from a .cmd or a .bat

this line ensures the correct working directory, which is the directory in which the binary file is located.
pushd "%~dp0"

and '%*' pass all the arguments to quakespasm.
quakespasm.exe %*

so, a .cmd script with this two lines
pushd "%~dp0"
quakespasm.exe %*