Boiler Replacement Questions from a New Homeowner

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After purchasing a 45+ year-old house, the ugly duckling on the block, my wife and I are looking to replace the original boiler with a more modern and efficient model. The house is a Cape Cod (2 rooms in a finished attic and 2 on
the ground floor , 1.5 bath with a full finished basement). Eventually, we want to put a shed dormer on the back of the house to expand the upstairs rooms and include a new bath. Unfortunately, I don't know:

1. what questions to ask when evaluating a heating contractor
2. What "the good brands" are of boilers
3. What I should compare when looking for a boiler
4. When the best time is to buy a boiler. Are there "end of year" or
"pre-season" sales or something?

Any wisdom shared would be greatly appreciated!
Thanks in advance!