Any thoughts on weather it is better to keep the building after the 27 +/- years or to build/buy something new? 

I'll be coming from Arizona, so I'm ready to embrace the polar opposite weather. 

The contract should include the start date, estimated completion date, price, reference change orders and/or allowances, and should contain some verbiage of penalty for delays within the control of contractor (weather, pandemic, etc. not in contractor's control).

I am making greater allocation to reserves and ensuring I am more resilient and can weather any storms that come (Metaphorically and also Physically living in Louisiana).

I can live in the property but do not have to.My question is, how can I find and gauge weather or not an agent is investment friendly and has access to off market deals?

Even if a professional roofer is scheduled, if weather is unstable, the roof may need to be tarped while waiting for the actual roof replacement. 

Still something to consider.Weather: Specifically changes in weather. the world is slowly getting hotter, and some southern states like AZ are so hot that you basically have to stay locked inside in the summer.

I can imagine some weather related damage but the question still is - is it too much work to invest in?

Occasionally they are inside the foyer, to get out of the weather...hot/cold/snow/rain....Probably most of the time this works, but obviously sometimes it doesn't.

@Clark Cannon If the margins are thin I'd consider having an extra cash cushion to weather any storms.