Installing ceiling electric box

Just wondering what sort of "gotchas" others have run into. Here's the situation:
Single-story home, built in 1956. Attic is easily accessible, although full of pink insulation. There's already switch at the room's doorway which controls an outlet. I plan on setting up the outlet to be constantly on, and using the switch to control the ceiling fixture. What I'm wondering is, how likely is it that between the switch box and the attic, the only obstruction I need to drill through (to drop the wire) will be at the attic level, as opposed to unseen wood that's JUST far away enough from the attic beams that a drill bit won't reach.
And: Running the wire across to the ceiling box, I'm guessing that code (and common sense) would dictate attaching to the side of the beam, not the top. Yes, no, maybe?
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Older homes rarely have fire blocking installed. Saying that you should be able to locater the wire comming up from the switch, ( most wireing is through the attic ) and using jack chain drop down to the switch box. Now comes the fun part. 1956 you probably have steel boxes. Open up an new knock out (ko) and then all you have to do is hit the hole. Might be a good idea to install the romex connector before you drop the wire down. A helper with a bright flash light helps. If you can not see light from above then your in the wrong spot or there is something in the way, (framing, insulation, god only knows). You may have to drill another hole for the new wire. I recommend an 3/4" auger bit for this. Yea 3/4" in over kill but you can see down the cavitity, at least I can. Is the outlet half switched or all switched? If it is all switched just change the make up so that it is hot all of the time. (just the hot wire everything else is ok) If it is half switched then your going to have 4 wires going to the outlet, hot,switched hot, neutral and ground. tie the hots together for on all of the time.
There are long speciality bits, (4-6 feet long) for remodel work. I have never purchased one as they are pricy. These speciallity bits come with an hole in the end. Drill down and then attach the wire to the hole in the bit and pull up.
I just cut in 2 recessed cans in the hall arches in my home. After I get done with the painting which is next they will look like they have been there from the beginning.
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Doug Kanter wrote:

Depends entirely on location, but there's a good chance you'll have fire blocks. This isn't good news, but it's not the end of the world.
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Well, one reason for asking the question was to weigh the cost of buying more tools, compared to having an electrician do the work. I just called 3 electricians. Holy smokes! They all said that if the jobs were nothing unusual, I could expect to pay $200-$300 per room.
I'm gonna find a source for the real long drill bits tonight, just in case. I doubt they cost $200.00, or $600 if I'm thinking of all three rooms. :-) It's those damned breather masks that are expensive, and the beer for after the job's done.
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... and I've seen people pay good money for work that I sure wouldn't be proud of.
... and while they do have an assortment of tricks & experience snaking wires behind walls, they have limitations too. You might wind up doing a little plaster / drywall repair no matter what. (Or you might luck out, too.)
You might consider one of those Time-Life DIY books on home electrical to get a better idea of how to get the job done. They're great books, well thought out, and could easily pay for itself.
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That's a good point. Some years back, an electrician installed a GFI in my bathroom, and managed to destroy about 2" of plaster all around the existing box. Now...I changed 18 outlets in other rooms, and figured out how to etch the plaster first so it came out in nice, clean slices. This electrician was about 70 years old. My first etching took an hour (meditation, thinking, 2 cups of coffee, etc), but the rest took about 3 minutes each. How come this ancient electrician didn't know this trick?
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