I find it helpful to think about the main reason Tribune required the restrictions.
Their business is selling this data. They want to allow hobbyists to play with applications and data, but they don't want any chance of competition with us for their own data.
I'll take a stab at your questions. (This is not an official response, just my personal opinion)
#1. It may depend on what the site does and how the data is used. If it includes Tribune's copyrighted text, I can see that being a problem. I don't think encrypting the data would make any difference since the data isn't distributed. (They're not concerned about someone hacking into a site to get the data). Remember Tribune owns web sites that use the data, plus they probably sell the data to other web sites that provide web services. Hobbyists with access to cheap data infringing on someone's "bread and butter" is a concern.
#2. A cloud based application that required each user to be a SD member is a grey area that I could see getting approved, possibly with some additional auditing requirements. The application site would have to be non-profit of course, no ads, etc.
#3.. not really a question.. I answered it above.
#4. Permitted by current rules.
Going back to #1 and #2, I've found Tribune Media Services to generally be very generous with exceptions (WiRNS for example). If it's a grey area and doesn't raise any of their concerns, it's likely to be accepted. If it's not accepted, they may be able to offer a viable alternative.