Anything left to interpretation will end up in court and then how will the courts decide ?

@YiBing T.What you are proposing is possible based on the interpretation of many tax attorneys, as outlined by @ George, but there is still some layer of risk if there is any perceived benefit between any of those plans.

Knowing how to read and interpret a contract is a valuable skill. 

If the law says 30 day notice, don't file until day 31 or better 32 just in case a judge interprets they way you did it differently than you.

Am I interpreting that 50% rule incorrectly?

There are agents selling properties (typically interpreted as a residential transaction) with the short term rental business attached (typically a commercial transaction).

Let me know if you interpret this differently.

Again, based on your interpretation of the situation, it seems like they are being unreasonable. 

You should also spend time at your local LTB hearing to get a better picture of how the board interprets the RTA and how landlords are treated.The most important advice is never waste a single day hesitating to issue LTB notices but make sure you do it right.

Any loan officers, or underwriters or even attorneys that can speak to creative ways that I may be able to meet this requirement, or if it is even applicable (based on how I am reading/interpreting it)?