Just looking for something that will automate my system to find, contact and follow up on prospective properties.

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I don't like buildings that are on boiler systems and $455k might be a bit high for one still on a boiler unless you meant water boiler for showers not for heat of unit.

Then you advertise and your marketing system should deliver you highly qualified leads in line with your business goals. 

Are there any systems or suggestions you would recommend if I was in the situation?

You can set up an irrigation system/timer for the entire property, and one zone could just be the foundation drip.

I was also looking at Attleboro (great school systems, people willpay a premium for that) and Taunton but Fall River and New Bedford seemed to be the best priced market and the ones that had the biggest chance at going up in value due to the train.

But it hasn't really touched the barely functioning mechanical systems that have been band-aided together for decades. 

Moving forward spend a lot of time looking up HVAC system, roof, water heaters etc.

The old tiered system has more or less been replaced w/ a new TOU (time of use) system.