to paint or not to paint?

Over the last month or so, we've been giving our house some major facelifts. Some of it was due to storm damage, and some of it was just routine maintenance. Our restoration work is nearing completion. The contractors have installed most of the siding, soffits, and fascia. Our new kitchen window above the sink is in. They've got a few sheets of siding left to hang, and then some trim. Then, we're going to have to decide whether we want to pay them to paint the house or if we should try and do it ourselves. I'm leaning towards just paying them for it. I've been falling behind on my web work lately. Since I feel I need to be available to answer any questions the contractors may have, it has been difficult to concentrate on programming. You know how it goes...you don't feel like getting too deep into it when you're expecting regular interruptions.

So I don't think I really have the time to take a few days out of my schedule to paint. As it is, we saved ourselves a chunk of change by putting the kitchen back together and painting all the interior walls ourselves. We also opted to just cover the existing siding, rather than have it all pulled down. This will save us a bunch of material handling, haul-away, and tear-down labor. I was leery about it at first, and hope that it doesn't come back to bite me in an inspection. Technically, there's nothing really wrong with covering the old siding with the new stuff. Most of it wasn't damaged; we only decided to replace the entire rear of the house so that it would all match. It just might look funny if someone got behind the trim and saw the two layers (extra R-value?).

Unfortunately, the way that the original builder nailed the windows on top of the siding would have presented some potential problems if we tried to remove it all. We'd basically have to take out all the windows, remove the old siding, install the new siding, muscle the windows back in and pray that everything opens and closes like it did before. No thanks. I can see that becoming a big expensive adventure. I'm also a little scared at what we may find behind the old siding. Every project that I tackle with this house ends up being one of those "tip of the iceberg" / "rust in a fender" experiences where we end up doing three or four times as much work as we had planned.