anchor roller install questions!

That was a frustrating waste of time! I bought a center punch and a set of "Titanium" drill bits from Amazon that had decent ratings:

http://www.amazon.com/gp/product/B000FK5GPE/ref=oh_o04_s00_i00_details

I made the measurements, found some 3-in-1 oil, and started drilling an outer hole. I started with a very small bit since that's the only one that would center on the center punch divot. It barely started making a dimple and then stopped making progress. I switched to a 5/16 bit and got a little bit farther, but same thing, it stopped progressing. This was after maybe 5 minutes on each bit of mid-rpm drilling with oil. Finally, I moved on to the 5/8 bit and it stopped making progress once the entire bit made contact.

What's going on here? I have a Milwaukee corded drill so no problem with power. I am thinking maybe I should just find a machine shop to do it.
 
This thread's been buried for a while, but I figured I'd add a photo of the actual install since I took a few pictures recently.

Here's the install of the roller and anchor. The hole pattern for the old roller didn't match the new one so I undercut and filled the holes with thin and then thickened epoxy. I drilled the new holes with brad point bits (in reverse until through gelcoat!), undercut with the dremel, filled with thin and then thickened epoxy, redrilled and countersunk (also in reverse!). I cleaned the deck and roller with acetone and then used butyl tape to seal it to the deck. The whole process is very well documented here:

http://www.pbase.com/mainecruising/sealing_the_deck

and here:

http://www.pbase.com/mainecruising/rebedding_hardware

I also drilled (using cobalt bits) through the roller base and pivoting parts so I could install a quick release ball pin to prevent pivoting while the anchor is stowed.

anchor.sized.jpg
 
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