In terms of local SEO, your most valuable and relevant backlinks are going to come from other websites and publications that are tied to your area.

I haven't been able to find anywhere post implementation of the laws that specifies exactly what they decided on in terms of enforcement."...other short-term rental property owners wondered how the city would enforce such limits.City Code Compliance Manager Joey Forgione said city employees would need a court-issued inspection warrant to enter a private residence and count heads.

Do you find that they are not flexible enough in terms of availability?

Try to get a good idea of where your property is in terms of what will be needed in the next year or two for both of those and work the numbers backwards.

Areas like Woodhaven and Richmond Hill have stayed mainly the same in terms of value, from what I've heard from home owners in those areas. 

How do I go about figuring out what all of the expenses will be in terms of "taxes, holding costs, closing costs (both ends)".

How does renting out a parking space differ from renting out an actual apartment in terms of costs, turnover, etc?

Or in terms of our deal....manage tenants. 

How much money are we talking about in terms of a deduction.

I don't know what markets you invest in but @Ned Carey hit the nail on the head in terms of places where wholesalers market their properties.