You may check out the nearby members and network https://www.biggerpockets.com/meet, it will help you a lot to find partners that can help you out in investing.

Divide those costs up over the remaining number of years of life for those major systems, and then add a bit more because while you may want the heating system to fail at the end of its life, Murphy's Law says it will fail years before then, so you better start saving.If you do go through the purchase, I would treat those capex dollars as spent dollars and put them aside in a separate account.  

Then - plan for capx like roofs, windows, driveways, siding, HVAC systems.  

There is a lot to consider: closing costs... potential agent commissions... fewer buyers if "Peter" decides to close shop and not execute the option (meaning carrying costs for you). 

Yes, the equity would help with the move, but we do have a small saving and good support system in place.

Has anybody (in the area, preferably) ever dealt with potentially rezoning a single unit lot to a two unit lot?

Who/what do you use for a system of checks and balances to make sure that your Manager is on top of renting/quick turns/collections?)

It is definitely possible, but you are have a lot to learn as a new wholesaler.  

Have you spoken, with the current Management Company, to ascertain if there is any existing maintenance that have been deferred such as roof replacement, window replacement, major electrical and plumbing systems, etc.?

I have access to off market deals and also use a system to track and purchase sitting MLS deals.