mmm.... not sure about this one.  In Finder, have a look in Documents, there should be a folder called SkyDemon, and inside that is there a folder called Charts? Is it empty?  If it's not there, try creating it and trying again. If it is there, try deleting its contents and trying again. 

Thanks for your Wineskin installer. Works on Late 2012 27inch i5 Imac 8gb Ram. updated to El Crapitan. Just sits there when trying to update charts though, progress wheel just spinning. Not tried printing yet either.

Regards
Ikarus
G-TIFG

it works. OS X 10.11 Macbook pro, early 2011, 16 GB.

Just checking - did you use winetricks to add dotnet35sp1 and gdiplus DLLs?
On my installation printing caused it to crash until I added the gdiplus DLLs - and then all was fine.

Alternatively, I've uploaded what I believe is a working version here:
https://www.dropbox.com/s/qp6xmsl6du6aa5z/SkyDemon%20for%20Mac%203.4.4.9.zip?dl=0
Download this, uncompress it, then copy it to your applications folder.
The first time you run it, you will need to locate it in the Applications folder from Finder and press the Control key, then click the app icon, then choose Open from the shortcut menu (this is because it is 'untrusted' - see: https://support.apple.com/kb/PH18657?locale=en_US )
This was wrapped using Wineskin 2.6.1, using engine WS9Wine1.7.52, and should run on Mac OS X 10.6 and above
I would be interested to know if this works.

Thanks for the hint with wineskin! I dared to go this way and SD works, but unfortunetly without printing. A long list of details which I´m overcharged with (debug problems?). No difference when trying a test run... Help from rikur?
Berlin, absolutely clear sky

I'd agree with that .... I'd speculate they'll announce at the WWDC in June 2017, for launch in Sept 2017 .... just speculation though.
 

Given that iOS apps now need to be resizable to work with multitasking on iOS, I wouldn't have thought it impossible that Apple would one day allow iOS apps to run on OS X.

There was an update to wineskin on 4th October which resolved the El Capitan issues - feedback in forums suggests it has been stable on El Capitan since then.
I've also worked in IT for ages - fortunately in progressive and successful organisations that understand the role that open source and wrapping have to play in software development.
I suspect this ultimately all comes down to money - developers cost money to employ; developers can either spend time developing features, or porting to other operating systems; you can employ more developers to try to do both, but then you have to charge customers more money; (and in practice you almost always end up with one platform lagging behind another and moans about lack of feature parity).  
Personally if it was my company, I think I'd look to do a good quality wrap of the PC version for the Mac and release it at least once a year in an easy to install manner like the old unofficial Skydemon for Mac version. 
I think your average Mac user in a flying club:
 - doesn't care whether it's coded natively or wrapped, providing it works
 - just wants it to install and run with one click of the mouse

Thanks Rikur,
I did the same and it works fine! But still  its poor not to have a native Mac App......
Anyway, thanks a lot!

I've just spent a couple of hours learning wineskin and have managed to wrap the latest 3.4.2.0 of SkyDemon to run on Mac El Capitan.
In a nutshell:
- download and install winery.app 1.7 from http://wineskin.urgesoftware.com/tiki-index.php?page=Downloads
- create a new wrapper using the latest engine WS9Wine1.7.52
- from the 'Advanced' menu use WineTricks to add dll package for dotnet3.5SP1 and gdiplus 
- Install SkyDemon (using the normal windows installation file from Skydemon website)
- (optional) under 'screen options' tick the first 3 boxes (Mac Driver, Decorate, Auto)

I now have a completely up-to-date SkyDemon running on El Capitan :-)  .... including printing, and so far it appears stable.
It was actually more straight forward than it looks.

A free and less bloated alternative to Parallels 
(I believe this was the same approach used to create the previous unofficial Mac version)

EDIT:  See later post on page 3 of this thread for a download of all the above