I have the same problem. Here are the steps I've followed:
Followed instructions to download metamod, sourcemod, CSS server and CS Deathmatch mod:
mmsource-1.10.6-windows.zip
sourcemod-1.8.0-git5967-windows.zip
cssdm-2.1.6-hg197-windows.zip (using the latest version I could find)
Followed steps 1-5 to download the CS server:
https://steamcommunity.com/sharedfil.../?id=397365275
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
http://www.metamodsource.net/
] meta list
[01] SourceMod (1.8.0.5967) by AlliedModders LLC
[02] CS Tools (1.8.0.5967) by AlliedModders LLC
[03] SDK Tools (1.8.0.5967) by AlliedModders LLC
] sm
SourceMod 1.8.0.5967, by AlliedModders LLC
To see running plugins, type "sm plugins"
To see credits, type "sm credits"
Visit
http://www.sourcemod.net/
Add in my Steam ID, which I collected by putting my profile URL in this link:
http://steamidfinder.com/
File I'm adding to: /addons/sourcemod/configs/admins_simple.ini
"STEAM_0:0:[truncated]" "99:z"
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

M 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.
Any thoughts?