Environment:
10.12.6 (16G29)8.0.11758a6ae7cautocmd StdinReadPre * let s:std_in=1
autocmd VimEnter * if argc() == 0 && !exists("s:std_in") | NERDTree | endif
map <leader>n :NERDTreeToggle<cr>
let NERDTreeShowHidden=1
Process:
mkdir -p dir_1/child_dir_1)dir_1 (ln -s ./dir_1 symlink_dir_1)file_1 in child_dir_1 (echo -n "dir_1/child_dir_1/file_1" > dir_1/child_dir_1/file_1)symlink_dir_1 and press enter to expand itfile_1Current Result:
Nothing happens at all.
Expected Result: _Describe what you would expect to have resulted from this process._
The file in the symlinked directory should open and allow for editing.
Additional Info
The same issues occurs for any directories within the symlinked directory. If you press enter to attempt to expand them, nothing happens.
This appears to be directly related to NERDTreeCascadeSingleChildDir. If it is set to 1 then I'm unable to enter symlinked directories or open files within.
Two things:
No guarantees here, but, if we can confirm the bug, that's a good start.
@lifecrisis: I just updated the "Process" section to include steps for the directory structure, but I've also included screenshots below.

NERDTreeCascadeSingleChildDir=1 results in not being able to access files/directories

NERDTreeCascadeSingleChildDir=0 allows for accessing files/directories properly
Well, you've done your due diligence here. Thanks!
I'll label this as a confirmed bug, but know that this is actually somewhat complex to fix. You'll likely have to live without cascading for the time being if you symlink a lot of directories. I don't know when I or someone else will be able to get to this.
I can't personally confirm on my own system (because I don't have a Mac), but I've had problems with linking directories on Windows, so this is clearly an area where the NERDTree needs more work.
Note: I just confirmed this on Ubuntu 16.04 as well. So, this is definitely a problem on all three platforms.
I can confirm this bug as well. Below is what I see with the 4 combinations of NERDTreeCascadeSingleChildDir and NERDTreeCascadeOpenSingleChildDir. There have been a lot of other issues related to these options, one of which appear to be a workaround for the other one. See #547 and #558. Plenty of opportunity to fix it once and for all.
let NERDTreeCascadeSingleChildDir = 1
let NERDTreeCascadeOpenSingleChildDir = 1
</junk/testing_symlinks2/
â–¾ dir_1/child_dir_1/
file_1
file_2
â–¾ symlink/ -> /Users/prunninger/junk/testing_symlinks2/dir_1/child_dir_1/
file_1
file_2
---------------------------------------------------------------------------
let NERDTreeCascadeSingleChildDir = 1
let NERDTreeCascadeOpenSingleChildDir = 0
</junk/testing_symlinks2/
â–¾ dir_1/child_dir_1/
file_1
file_2
â–¸ symlink/ -> /Users/prunninger/junk/testing_symlinks2/dir_1/child_dir_1/
---------------------------------------------------------------------------
let NERDTreeCascadeSingleChildDir = 0
let NERDTreeCascadeOpenSingleChildDir = 1
</junk/testing_symlinks2/
â–¾ dir_1/
â–¾ child_dir_1/
file_1
file_2
â–¾ symlink/ -> /Users/prunninger/junk/testing_symlinks2/dir_1/
â–¾ child_dir_1/
file_1
file_2
---------------------------------------------------------------------------
let NERDTreeCascadeSingleChildDir = 1
let NERDTreeCascadeOpenSingleChildDir = 1
</junk/testing_symlinks2/
â–¾ dir_1/child_dir_1/
file_1
file_2
â–¾ symlink/ -> /Users/prunninger/junk/testing_symlinks2/dir_1/child_dir_1/
file_1
file_2
It's been a while since I've looked at this. A solution wasn't too hard to implement. Check out pull request #914, and see if it solves your issue.