Tenants do not have a choice as to what they pay and it is not negotiable.

I did raise one tenant a much larger amount but that was due to them having below market rent. 

Values are determined in July of the previous year, and properties are rarely visited in person by provincial appraisers.For this reason, provincial property assessments should never be solely relied upon as any sort of relevant indicator of true market value for the purposes of purchase, sale or financing.Think of the assessed value instead as something akin to a weather forecast, spanning far larger and more diverse areas than the unique ecosystem that is your neighbourhood, your specific street, or your specific property.

Be prepared to have fewer closings than a residential agent would be used to but the commissions are higher to make up or it, if you're targeting higher priced assets.The experience you will get in learning the transaction process, the due diligence required, and the financing strategies to get the deal closed will be better than any training from a Guru because you're in the transaction and learning it first hand.As far as tools, yes they're more expensive in the commercial world, it's just a cost of doing business, get's you larger to deals to make up for the expense, and lowers your overall tax bill at the end of the year.

A larger suburban home will want the 36"-42" depth. 

Our goal has been to actually keep this primary property and rent it out and purchase a larger home but we wonder if we had two properties appreciating at the same time with one giving us some serious tax advantages if that would be a better strategy? 

Or church or anywhere else in the city other than your place.I would cancel this booking immediately and rethink the instant booking choice.

Good choice!

Our broker is making it sound fairly black and white - that if they show proof of funds/financing, the Seller has no choice but to accept the first offer and move forward with them. 

Lease to own and seller finance traditionally both require a larger downpayment.