The first thing you need to do is address the leaks--are they all from the siding, or are there roof issues? Leaks around windows could be from improper flashing, not just the siding.

Putting siding over the current shingles will not stop the leaks which already exist--it will just hide them.

You have another issue to address--you'd better find out what the local zoning requires. In our town, if it comes to the attention of the building inspector that a home has asbestos siding, they require the owner to have it removed and replaced. Happened to a neighbor of mine--expensive proposition. And really, it's something you want to get rid of sooner rather than later--just because it's in good shape today, doesn't mean it will stay that way. A few kids with a basketball....

Anyway, check with your building codes before making your final decision on what to do.

Asbestos aside, given the numerous problems you're having? I'd want to have the house stripped, adequately protected and re-sided anyway. Sounds as if it's time, and that by doing the occasional patch job, you're just putting off the inevitable, and the price of that job is only going to go up over the years (inflation, etc).

azzalea-
Can you clarify something? Do you mean that a building inspector in your town can just come by and order removal of asbestos siding on a house where no construction is underway? In my experience in a number of communities, building inspectors can only require that a home (or part of a home) be brought up to code or meet some new standard if the homeowner is actively remodeling and the area being worked on relates to those requirements.

Kudzu--yes--the house was having NO work done, and someone from the township came by, walked around, and next thing you knew, the neighbors had a letter giving them a time frame during which they had to replace the asbestos siding.

Thanks for the info. That's pretty incredible. I'm all in favor of minimizing risk from things like asbestos, but when it's undisturbed it doesn't seem fair, necessary, or perhaps even legal, to order a removal. I wonder if anyone has ever tested this by filing suit against the town. I know enough about asbestos regulation (having worked in this area for many years) that this certainly doesn't derive from any Federal law or regulation or probably even a State requirement.

It's pretty much the same kind of thing as a weed letter, I imagine--when a township official can send a letter requiring a resident to cut their grass or face stiff fines/penalties. That's done all the time. I don't really see why you would say it wouldn't be legal--if the town has specific requirements, as is their right, it would be legal for them to enforce them.

Of course, I live in New Jersey--where pretty much everything we do is regulated, controlled and taxed by either the state, county or local governments--sometimes all three. And don't even get me started on what our state EPA has done to people I know....

azzalea-
It's one thing for a person to let the weeds grow waist high or let junk pile up in the yard. In that case the property is being allowed to become an eyesore, and it's understandable for a town to want to prevent things like that.

However, it's another thing for someone to make me undertake a remodeling project at my own expense. If I have old knob and tube wiring, the building department can't force me to bring it up to current code if I'm not remodeling. They can't force me to make changes to my plumbing, like adding shutoffs to sinks and toilets if I'm not remodeling. And they would have a very difficult or impossible task to claim that my undisturbed asbestos siding was posing a threat to anyone. They may have such a requirement in place, but it doesn't mean it would pass legal scrutiny if challenged in court.

The siding is not the drainage plane anyway.

The layer of felt underneath it is.

You need to investigate why the drainage plane is failing.

One reason would be gaps in the siding allowing sunlight to hit the felt paper.

The siding is there to protect the drainage plane from damage (including UV damage from long term sunlight exposure).

A this point you may have to strip everything and start over.