I have the same problem. Here are the steps I've followed:
Followed instructions to download metamod, sourcemod, CSS server and CS Deathmatch mod:
cssdm-2.1.6-hg197-windows.zip (using the latest version I could find)
Followed steps 1-5 to download the CS server:
Followed instructions to unzip metamod to CSS/cstrike addon files.
Started server using shortcut, run as administrator, using these parameters in the shortcut:
"C:\steamcmd\CSS\srcds.exe" -console -game cstrike +maxplayers 32 +map de_dust2
I then open up my CS game from Steam, join the server, can type meta version in the console. I see that metamod is installed and running, so I exit and follow the instructions to unzip the sourcemod.
After copying the files into the cstrike folder, I restarted the server, join it from CS, and run these commands:
] meta version
Compiled on: Sep 10 2015
Metamod:Source version 1.10.6
Plugin interface version: 15:14
SourceHook version: 5:5
] meta list
 SourceMod (126.96.36.19967) by AlliedModders LLC
 CS Tools (188.8.131.5267) by AlliedModders LLC
 SDK Tools (184.108.40.20667) by AlliedModders LLC
SourceMod 220.127.116.1167, by AlliedModders LLC
To see running plugins, type "sm plugins"
To see credits, type "sm credits"
Add in my Steam ID, which I collected by putting my profile URL in this link:
File I'm adding to: /addons/sourcemod/configs/admins_simple.ini
Then I restarted the CS server.
During play I could run sm_admin and also bind it to a key.
After that I copied the CS DM mod files to the /cstrike folder.
Restarted the server and rejoined it.
Upon trying to join a team it crashes upon spawn.
I reloaded the server and client again, but this time would play.
But when I attempted to add a bot using bot_add 1, and the slayed myself (to restart the round and allow the bot to spawn), it crashed.
I am running the shortcut as administrator within Windows 10 and I also removed the read-only permission from all files and folders.