I read somewhere that the owner doesn't get penalized if the "legal/illegal" unit stays occupied and you can continue renting them out, and that they lose the rental privilege if they're vacant for more than a certain amount of days.

(Renewing a lease is a privilege given to residents that abide by the rules and are not a PITA).

Is becoming an agent for a few years then gaining my brokers license the only way for me gain the privilege of buying and selling properties or is there some unconventional method that I missed?

Most accountants, CPAs, and tax professionals will be very familiar with it and it is pretty easy to give them privileged access directly from the program.If the setup is done correctly, we should be able to reduce your time from six hours of data entry to an hour of reviewing the details every month.Let me know if you want to discuss and we can assist with setup.

When they request to review the document they will need to deal with attorney-client privilege, which can be a daunting and expensive task.

@Allen GregoryIt sure seems like you’d be asking the Attorney to violate Attorney/Client privilege.

And of course other terms will be stated here.ON the option to purchase TERMS: The Tenant/Buyer, as part of the consideration herein, is thereby granted the exclusive right, option and privilege of purchasing this property at any time during the term of this Lease/Option agreement.

The two additional benefits would be that the Land Trust would be easy to tie into any future estate planning you do and you could also add an additional layer of privacy by having your attorney sign as a "nominee trustee" and so your name would only be visible on a private document for the Land Trust protected by attorney-client privilege (so people can't just search you out without paying significant discovery fees.)This is just a brief explanation of this option, so if you want to know more be sure to just reply and I will swing back next time I am on BP.

I paid him 125k for the privilege to step into his contract. 

So they are willing to buy an option to purchase the property and they are willing to pay a little more for the property per month for that privilege.