Your best chance at securing a multi family will mostly come through an off market deal. 

You may have neighbors willing to help now and then, but it's unlikely you'll find a neighbor willing to do this all the time, every time, for years.In my experience, most landlords lose far more money through self-management than they would by hiring a professional, even when they live close to the rental.

IMHO and all things being equal, this route would be the fastest way to cash flow and scale.  

I re-read it about 3 weeks ago and spent time working through the steps as outlined in the book and this time I got really excited about it.

It looks like there are some properties priced in this range, but they will not cash flow.

They work with business owners and they walk you through how to set up and optimize the PM company, etc.

I have done a few of these last year and all (3) of them came over to me from a realtor who was trying to find a bank to fund.If you do not go through the right bank or program you will pay earnest money, commit to contract, pay for appraisal and end up getting the loan denied in underwriting.

Each unit in teh building has their own master water shutoff valve, so I can't imagine it will be that difficult to get some hardware + automated billing system through someone.

Assuming you're contracting it out make sure you get multiple bids and I'd do the bare minimum inside or do that yourself (unless you're going to make it a hangout spot as a feature for guests - could also do this over time as you see increased cash flow).

John/Jane Doe, and any change in occupants requires mutual agreement of both parties to ensure that the business doesn't start to rotate different employees through with no option?