The attorneys I have worked with when buying a large apartment complex have all recommend one LLC for holding the property and one for managing it.  

In the end, it cancels out any benefit.Loss of Key Homeowner BenefitsIf you sell your home to an LLC or S-Corp, you’ll lose:$250k/$500k capital gains exclusion on selling a primary residence.Homestead exemption on property taxes.Owner-occupied insurance rates, which are cheaper than rental insurance.Substance Over FormIn tax law, the IRS looks at the substance of a transaction, not just the form.

I'll work with an attorney to assist with drafting that.Q2: Yes, I'll talk to my CPA but we'll most likely hold the property for at least 1 year under the LLC given our timeline to design, permit, build and sell the property, meaning I should avoid short-term capital gains.  

There is no mortgage on the property.   

Looking for points of view on selling or keeping properties in Toronto, Ontario.

My advice: Sell ALL of the small stuff ASAP

If they fail to pay the taxes, plus fees and interest, within that time, then the property legally becomes yours.

I am looking to add a 2nd investment property to my portfolio but I have no cash to do so.

Especially on a rental property. 

You could also put both on the market and see which one sells first and then cancel the 2nd.