Use a reputable firm for the VA, obviously.

You could contact a local reputable commercial broker and determine if this property truly has value but do not waste their time, if they help you then give them the listing to lease the property if you end up purchasing. 

Rent to own has gotten a bad reputation in some circles since the renter/buyers rarely wind up acquiring the property.

Hey @Dylan Bard just talk to a reputable real estate attorney about structuring a JV, not a syndication, to tackle a property together.

We have known each other a little bit for years as we are both in the construction trades with great decades long reputations.

Yes  they don't really have a nonA list the pilots are expected to find thier own and most of this is word of mouth but explore altuspilotsuites and let me know what questions you have after and look for something similar in Tampa I know there are a few

I would, however, love to explore areas within the GTA that could have that strategy applied to it.

I would not have rentals in some states and regions and if I lived there I'd explore other options.

I always advise my clients to explore a HELOC before a cashout refi, origination is less, HELOCS can be reused once paid, and if you wont have to take the rate hit that comes with a cashout refi. 

@Austin Adams I recommend taking your time to explore the different areas and communities and refine your criteria before you pull the trigger.