Moved to Installation/Hardware/OS as it also covers Licensing and it therefore more appropriate.
"Checkout" implies Network Licensing which wouldn't normally be used with the trial AFAIK.
Can you post a screenshot of the error please?
If you get no further responses in a day or so I'll PM someone who should (hopefully) be able to help.
Max 2016 (SP1/EXT1)
Win7Pro x64 (SP1). i5-3570K @ 4.4GHz, 8Gb Ram, DX11.
nVidia GTX760 (2GB) (Driver 430.86).