Staples?? Use the nails as mentioned. It's good advice. End of discussion. It doesn't get any simpler. BTW, "eyeball" it as you go along to keep it nice and straight/tight, etc. Better yet, use a 4' level every once in a while. A block of wood and short length of 2x4 can help to adjust it, too. This post was edited by homebound on Fri, Jun 21, 13 at 20:31

@ Caterina's post. The beads are metal ,probably sat exposed during construction , the stucco isn't covering them all over , and the paint isn't going to do all the heavy lifting on it's own.Maybe some attention to the beads before painting would've prevented this. It gets so bad here in Florida that the beads actually lift out and water gets in them. Here's an example before it's started to wear and rust... I have used a textured elastomeric patching compound to float over all of these areas and match the finish with success. Some knife grade patches work very well. I'd clean and prime the rusted areas with a alkyd or shellac primer then cover everything with elastomeric patch textured to match then prime and paint....Should last...It's rubber.... even the paint is rubber based usually...I don't have a finished picture but, you should get the idea...

I think the neatest way to do this is to run the cables into an outlet or light switch box, and when you've done your repairs you can then put a blank light switch type cover over it. There's probably a rule in regards to the nicked insulation, but it'd have to be really superficial to just wrap with tape. The tape would have to be wrapped at least as thick as the original insulation, so it won't be pretty - and possibly not legal. The only consideration is whether you'll have enough slack to cut the cables and join them, and you are right, the joins need to remain accessible.

There are several things that could be done better here, but as far as your original question, no, there is nothing wrong with the siding butting up to the window trim as opposed to overlapping. In fact, it is preferred. The other items of concern have been mentioend above (drip cap, trim boards are not thick enough to provide a clean caulk joint, the way that the trim boards are installed, etc). It doesn't strike me as a professional job.