Currently have a lot of investor clients who range from a new investor with one condo to large commercial clients with multiple apartment complexes and commercial buildings.Not sure where to start, so I figured coming in slow would probably be the best bet and gather thoughts about what direction to go. 

Do I have a attitude, you bet, can't collect from them when they default and 80% will be a problem guaranteed.The vast majority on welfare of any type in Ontario are scammers stealing tax dollars and all believe they deserve every cent they receive.

I figured it would be my best bet with what I am starting at.

Step away from this nonsense.Unless she has a source of income to actually buy this, that she hasn't declared to the local housing authority, I will bet that she wants to use her Section 8 deposits to  you to purchase the house. and if she hasn't declared her extra income to section 8, then she's just defrauding the system.You can either say "no" directly to her, or just say that you still have a mortgage and you can't enter into a lease purchase agreement for at least another 12 years.

I know that leaning on the idea of appreciation veers toward speculation, but in Westchester its a pretty good bet that the property will appreciate pretty significantly. 

I bet your local McDonald's isn't running on a MTM lease.

I am a fan, just not of the president heheI bet you a dinner at Mancy's that it won't take affect on August 16th?

So if you're interested in placing tenants then your best bet is to get your agent's license and then find a broker or property management company you can work with.  

I personally think some of the areas of the county that were previously very rough but are gentrifying are your best bet.

A conventional loan is just a standard loan like you're getting to purchase the rental.The Executory contract sounds like your best bet based on your goals.