I replied to your email earlier. Cloud does not support Boss yet. We plan to start adding more sites to cloud cash game support in the near future based on their popularity and plan to eventually support all the same sites that HM2 supports. Once we have all the sites supported we will begin work on adding tournament support.
Even with cloud, if the problem is your site folder where the hands are supposed to be wrote is read only, you may still have to edit the permissions for that folder and possibly for the cloud programs folder. The only difference would be you wouldn't have to do it for the postgresql folder since cloud doesn't use PSQL. The permissions issue you are referring to is a Windows issue (that is more of an issue in W8 than in W7) that affects all trackers pretty much equally.