I removed the Windows features for old SMB, rebooted, tried mapping with IP and it worked. Thanks!

Will take a look around, thanks. Just to be clear, I don't have an es_systems.cfg in the directory right now, doing that will cause it to appear so I can modify it? Sorry to clutter the thread, I'm still pretty new to this stuff. I'm running the latest version of RetroPie on a 3b+, if that makes any difference.
Edit
Should have clicked the link before responding, all good now! Thanks for the quick response and help

SSH works. I can go into my terminal program and SSH into the pi just fine. But when I open CyberDuck (my FTP/SFTP client) and try to connect, it just times out. I have not changed the default password.

Are you sure you're using SFTP/SCP as a connection type ? FTP would not work with SSH.

When I try to connect to the SMB share through Finder, it won't accept my password.

Have you tried as 'Guest' ? That should work also - no problem using that on any version of RetroPie/Raspbian.

That's not going to work, it's how CIFS/SMB works. You can't mount a host, just a share. Sure, the file browser shows you the available shares, but even on Windows (using Map Drive) you can't do that.
Maybe there's another solution with an intermediary program that reads the shares and mounts them separately so you can see them side-by-side, but underneath mount will still only map each shared folder.

@BuZz I feel like an idiot. Thanks for the help

Welcome to the forum.

@ammowaste said in Roms on a Network Share. Challenge accepted.:

permisions are okay.

How do you check that? Care to show them to us?

@mediamogul Yeah, I have to wonder if something in a kernel update caused things to get funky.

For what it's worth, while adding this week's MAME ROW games to my system I updated to 4.3.15 (07d9f95) and it didn't resolve the issue. I'm hoping either reverting to a really old version of RetroPie and then just not doing any updates, ever, or updating to the new Stretch version will resolve the problem. I haven't made the time yet to disassemble everything and put a different card in to try that route.

@drake999 Follow this guide instead.

@DanielMedStortD I believe so. Just have to try it and see :p

@sselph That looks great, I had no idea it would work that way!

Disregard the rest of this message. I found the solution on the Raspberry Pi Forums. Again, surprised it doesn't have anything to do with network shares but the solution will be the same.

In case someone else stumbles on this post and wants to know the solution I'll be going with; I'll be editing the savestate and savefile directory in the retroarch.cfg file. We'll make this a local destination and worry about space issues if/when the time comes.

I have another problem. I was apparently wrong about it being able to save to the share. The save files I saw in there were all from before I set it up this way and they don't update as we make progress.

When I hold Select + Right Shoulder, it says "Failed to save to /home/pi/RetroPie/smb" or something to that effect. I'll have to play with permissions and stuff on my Windows machine tonight but any advice would be greatly appreciated.

It's weird that I'm not finding anyone else that did a setup like this. It was one of the first ideas I had before the RasPi even came in the mail. Hopefully I'll get all the kinks worked out and write an all inclusive guide for it. Would love to see it put up on the wiki someday! :)

I take that back, I see where a couple of people touched on the subject and maybe more on Reddit but I can't access it at work :(. The one I was able to read barely got as far as I have and made no mention of issues with saving. I'm guessing it wasn't a problem because he was using NFS but I've never played with NFS shares so I can't speak to that.