Hey @madleine,
thanks for reaching out.
The “WordPress can not make requests to itself” issue should be gone once you update to 3.1.5 – I noticed that LocalWP no longer sends a response for our check, so the check always resulted in false.
We now check if there is an error within the response, and if not, the test is valid.
Ensure the SSL certificate is trusted by LocalWP (you can check that by looking at the project within the LocalWP app).
Also, ensure you have multiple sites linked somewhere (via a menu or sitemap) so Simply Static knows about all the pages/files to fetch.
I would also recommend enabling the debug log (Simply Static->Settings->Misc->Debugging Mode) – on your next export, you will see a download link on the “Generate” page – open the file, and you will see exactly what causes the problem.
Cheers,
Patrick