So it is critical to work with a broker who thinks like a real estate investor. 

From our experience if it was not a property deficiency or operational failure caused by the property or outside source (neighbor or rando)- the tenant is liable for the charges- property management or vendors sent to resolve the issue may troubleshoot the issue to help the tenant avoid these no work done maintenance charges.

Regarding source of funds, I would use the money in the brokerage account first.

I am 6 mos away from using other finance sources. 

@Patrick Orah Specific to your difficulty in finding a handy-person, have you tried using services such as Angi or Thumbtack to source some based on reviews of their previous work within their community? 

You need an inflow of cash from an outside source into this situation to work for everyone.

I am using Facebook and another roommate finder app to source for roommates.

Most landlords like to see job stability and you being the main source of income having a brand new job will be of concern to many landlords.

A call to a town building department, or an internet search should answer that for you.2) I have found The Journal of Light Construction to be an excellent source of information.

Timing is critical.