An old home, and lots of questions

Q. We have a turn-of-the-(last)-century front-porch colonial. It needs substantial modernization, and I've found that problems that seem unrelated in fact do contribute to one another, leading to bigger costs than expected. For example, we need a new boiler, new wiring, a rebuilt chimney and insulation in the walls. Further, the house has a lead water main and a sewer line that has been penetrated by tree roots. The boiler connects to the chimney, which has never been lined and doesn’t have a rain cap. To replace the boiler, we have to line the chimney with a liner that fits the new boiler, and we have to rebuild at least part of the chimney above the roof.
I'm tempted to decommission and dismantle the chimney. I've heard there are boilers available that can bypass a chimney and vent directly outside the house. Are these types of boilers much more expensive -- and are they permitted under code? If we install a boiler and water heater vent outside the house, will taking the chimney down detract from the house’s value? If a roofer patches over the hole, will this be unsightly?

A. I’ll answer all of your questions, but it’ll take several columns. I realize that you’re overwhelmed by the challenges of moving into a charming old house to discover the pitfalls of your new “money pit.” You’ll spend many days and nights wondering why you didn’t just pass on the deal, followed by rationalizations that “they just don’t build homes like they used to.” My response to that cliché is, thank goodness!
As an owner of an older home that needed updating of nearly everything, from drafty windows to a lack of insulation in the walls to under-structured floors, and with surprises at every turn, I opted to make major renovations and additions, essentially starting over. I have encountered countless owners’ dilemmas over the years, and can only suggest that you develop a serious written plan of attack, keeping the financial part of your plan as up front and realistic as possible.