 Steam pipes must be insulated to keep the steam from condensing before it reaches the radiators. In the old days, we used asbestos. Nowadays, we spend a lot of money removing the asbestos, and we rarely replace it. Most folks figure the heat isn't "lost" because it's still inside the house. But if the steam is condensing in your basement pipes, it won't be condensing in your bedroom radiators on the second floor. You'll be burning lots of fuel and you'll be miserably cold.
If your steam supply pipes are uninsulated, have the contractor include a price for new insulation. Or insulate them yourself. You can work wonders with a few rolls of fiberglass insulation and some duct tape. It may not look pretty, but it works well.
Reputable boiler manufacturers include cleaning instructions in their installation-and-operating manuals. The contractor must follow these instructions if your new boiler is to make dry steam. Have the contractor show you these instructions, and have him write on the contract that he will follow them to the letter. Then make sure he does.
It takes nearly a full day to properly clean an old steam system. There is no chemical or magic potion I know of that can make decades worth of dirt vanish. Don't accept shortcuts.
Have the contractor install a drain valve in the boiler's mud leg. The mud leg is the drum at the very bottom of the boiler, the place where sediment will gather. If you don't insist on this drain valve, you probably won't get it. Most contractors will leave the drain valve out to save a few bucks, but without it, you won't have a way to flush sediment from your boiler as the years go by. Dirty boilers have shorter life spans than clean boilers.
 Get the contractor to inspect your air vents and replace them if necessary. You'll find these air vents on your radiators (if you have a one-pipe steam system) and near the ends of your mains (on both one- and two-pipe steam system). Good air vents make a dramatic difference in system performance. Even a brand-new boiler will gobble fuel if the air vents are old and clogged.
Be prepared to pay extra for the vents. But take some comfort in knowing that this is one of the best investments you can make in your old steam system.
Heating contractors buy their equipment from plumbing and heating wholesalers who handle specific brands of boilers. Since the wholesaler extends credit to the contractor, the contractor will usually buy what the wholesaler stocks.
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