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I am going to build a bedside table with this sort of design.

My question is this: Should connect the outside wood by drilling Kreg holes on the main inside wood, Or should I go from the outside in?

 

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I would Screw from the inside to the outside.
I agree with Al.
I think putting the pocket holes in the center piece would look the cleanest from the outside and under neath. The holes may be visible if you put them in the outer pieces depending on how wide the border pieces are. I think the pockets the kreg jig makes are around 2" long.
I would put in two biscuits in each joint (space permitting) and 'Kreging' 1 or 2 screw from the underside. - CAUTION - In the past I had some problems with twisting at the joint and solved this with constructing only one corner, weighting or clamping it flat, and waiting 24 hours for the biscuit and joint glue (tightbond lll) to dry. Takes longer but the results are perfect. 'bob the builder'

I made these end-tables out of quarter sawn oak.  The picture frame design worked well and tightened up the seams of the 45 degree miter on all four corners, but the frame had to be approximately 3.5 inches in width, and the Kreg Pocket holes had to be positioned carefully, so that they were not exposed when looking at the underneath side of the lip edge of the top.   Pocket holes could then be used to fasten the "box" to the top from the inside.  I am going to look into the micros kreg screw system to see if I can shorten the length of the pocket holes for application like this one.

 

I also used pocket holes to join the four pieces in the center to create the unique pinwheel effect of the woodgrain insert.  I later added tempered glass inserts to protect the insert finish.

I believe if it were mine, and I lived in an area where there is a wide swing in humidity (which I do here in the north east), I'd make the top more like a cabinet door with a tongue and groove type of construction and use the Kreg screws on the outer frame only to hold the corners together.

With the configuration of your project in the photo example, the bedside table top will expand and contract the most in the left and right directions (across the width of the grain) and might cause issues if you have the main top screwed with the pocket screws to a point that they restrict the movement. This is why door panels are made to 'float' within the door frame.

A slot cutting bit on a router table will work fine for the 'groove' if you don't have access to a table saw.. and most likely you have several different bits that would work well for the tongue part...

Yes it's true that the expansion 'should' not be that much, but why take the chance after doing all that beautiful work..?

Just another point of view....

Ez
great project..do you have a working set of plans.  thanks..well done

Sorry, it was one of those build it as you go type of projects.  I did sketch it off on paper, but nothing of good enough quality to be called a working set of plans, but I ha ve been thinking about working up a set of drawings for several projects that I have worked on "perfecting" , so I might give it a try... 

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