Sounds like a nightmare just waiting to happen. I have heard horror stories about the stupidity and politics that can happen in a small condominium or town house complex. and a duplex is the smallest complex you can get. Bigger owners associations don't seem to have as many problems, although they still have some. Just imagine the stupidest most obnoxios person you know moving in next door. and now you have to deal with him when the house needs painting, or repairs, or even the lawn mowed. He doesn't want to pay for anything, or he insists on the half a__ed cheap fix. You can't aford to take him to court every other week, you can't even sell your half because he has trashed his half and sits on the front lawn in his underwear drinking beer when you try to show the house. My apologies if I have described any of the regular posters here!!

Estimate for Hardie? I didn't but only b/c we got got the painting done for "only" $8k (note that I have a dutch colonial: brick 1st floor, only painting to be done was 2nd floor (white cedar shingles) and tiny kitchen porch railings and 6 window shutters.) This was after estimates for $15k and $12k IIRC. If we were planning to stay here long term I'd definitely reside next time. (Would research to see whats new first. There's a faux cedar shingle called "Cedar Impressions" another 1920s house used. They also have color choices like Hardieboard. That home looks new still - been at least 5 years since they resided. In another part of my town with tear downs/new construction: all have composite siding - so I'd go find out what they have. I don't ever see new builds with wood siding here.) As I get older anything I can do to make maintenance easier/less often is worth considering. I'd guess that the labor hours for residing is similar to that of painting - so probably wouldn't cost that much more. (Labor is, by far, the biggest cost to paint - sounds like in your area too as goodness knows paint doesn't cost $15k.) But finding a skilled carpenter is probably harder than finding a painter here.

Engineered is hardwood applied to a good quality plywood. I liive on Cape and engineered is the only way for you to go (in the wood family). I copied this from the Spruce blog; Engineered wood is better than solid hardwood at dealing with moisture. Its plywood base is dimensionally stable, meaning that it warps and flexes less easily upon contact with moisture than solid wood. Fibers in plywood run in cross-wise layers, a far more stable structure than solid wood's parallel fibers. We owned an 1820 half Cape. It came with original wide plank pine floors which were in tough shape. My builder flipped them over and had them refinished. Gorgeous! Next house, same neighborhood, 200 yds from the water. This house was new build and I chose Homerwood engineered hickory in Saddle (refinished, no mess, and no guessing about the color). Gorgeous! 100 yr old cottage sounds so old to someone young, but 1919 is pretty flexible for design, unless you are talking about a distinct/authetic design vintage home. Choose what you like, but that close to the water…go engineered. It won’t cup and you can wet (wrung out) mop it when needed. Use Bona. Our present home, not Historic and came with a pool, I used wood look white porcelain. Gorgeous. Love Newport..my daughter is Navy…Thames for food and shopping, yeah!

Thank you all for your comments. I am still so torn because the trim on the siding is rotting away, especially on the back of the house that faces north. Granted, this wood is probably 25-30 years old... I am concerned that it will begin to rot again, when new wood is replaced. Our window sills are rotted and even windows are rotted. I assume this is from rain and maybe it can't dry out enough on the sides because the houses are close together? I just hate to waste a huge chunk of money on painting/staining the existing siding and have it all go to waste. It is going to be $18k to do the hazmat removal of the lead peeling paint, replace rotted wood and then put new wood siding on the addition. It's not like this is a $5000 job... Another concern is that I just found out a lot of moisture gets into the walls and seeps out of the house? Is this true? From cooking and showering? So this can cause the paint to fail prematurely if there is no vapor barrier, which there wouldn't be, since the cedar is original to the house in 1918. I also have concerns about going over cedar with vinyl for the same reason. I am concerned that mold could build up under the new vapor barrier that they would put up... I remember one siding company said it is a bad idea to not remove the old siding and this may have been why. We have had issues with mold in various places like under the front porch, but once proper ventilation was installed, it went away. I just don't want to have everything sealed up to the point that no water vapor can escape and is encapsulated in between the layers of siding, causing mold growth. I'm probably over thinking it, but we are stuck in which ever direction we choose, and neither is "cheap".