This thimble transition coming from the oil fired boiler and exhausting into the chimney flue is very important, there should be no gaps or holes present. We inspect these to make sure no dangerous gases are escaping into the house.
New England homes tend to have water/moisture basement issues. Here we can see rust on the exterior of this lally column and is a sure sign of basement moisture. We suggest if you notice metals rusting in your own basement to install a dehumidifier.
This is a common issue we come across at our inspections. Here is a basement drain not currently being used and could potentially release harmful gasses into the house. We suggest capping this off immediately.