If you see white smoke streaming out of your chimney when the boiler is running, it is time to replace it. While your at it, you might want to take a look at "greening" your system (if it is an old steam boiler), to save you some cash in the long run; i.e. newer piping techniques and insulation. New boilers are much smaller and have very specific piping that needs to be done to dry out the steam and not waste fuel trying to push heavy wet steam up the piping. Hot water might not be as fussy (I have an old 2-pipe steam system). If you have steam, take a look at heatinghelp.com it has a ton of info on how to get the most efficiency out of a system, and can give advice on both DIY or finding the best pipefitter. They also offer help with hot water, but I don't have any personal knowledge of that forum. When we bought our home, it had a new boiler, but it was piped way wrong, so I had to replace all the near-boiler piping, but it's been running great ever since.