Don't let formalities hold you back.  

There is definitely a need for them to develop a formal onboarding process.

He is not formally a property manager.

I don't personally play a lot, but others on my team love it for recruiting and networking because it's not as formal as even sitting for coffee.

The city will need plans, blueprints and possibly a variance to give you formal approval/issue permits (that's the part that the contractor and/or architect handles) but if you can give them a general idea of what you have in mind they should be able to at least tell you whether its feasible or not.   

I am going to say this and when I do it is not purely out of self interest.Note Newbies need formal training. 

I recommend some more formal business oriented options below:cozy.co - website with no fee rent collection service- no fees for either party. newer entrant but seems trustworthy and user friendly. haven't used this yet.https://www.biggerpockets.com/forums/92/topics/198046-cozyco-reviewshttps://ipn.intuit.com/ - Intuit payment network- 50 cent fee per transaction and can be recurring payment. reputable company and relatively easy to setup.

It is a formal transfer of responsibility to a new borrower.

Then they used lowball comps, which I had to protest (you only get 1 protest), and I did not want to spend the $$$ on a formal appraisal, which is an option if you so desire.Here's the kicker, the XOME number on their site, because they are trying to be like Zillow with an estimate, was much higher than what I got from the XOME appraiser.

@Cody Wageman- thanks - best   first  step  will be to  get  formally pre approved  with a  lender  for  whatever  hypothetical  scenario for the  rental purchase  you want to  work with ...this will insure you are  able to  get  financing for the  property plus  it will educate  yourselves  with the process and the  present  numbers   ( payment / rate / cash needed for closing  etc ...)