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I've drilled some long applications. About 8' is the longest, and never
with the size cutter you are talking about. Depending on what you are using
for extensions gravity can be a factor also. Break out may not be all that
important depending on the application, but all bits I have used experience
break out in wood. Some worse than others.

I have lost bits and extensions inside walls and other spaces. That is
something to be avoided if you can, but there are a few of my bits still in
some of those places.

Given that you are making multiple holes through 2 by you will want to
consider that the bit will dull slightly after each penetration. To
minimize breakout you will want to have a couple bits or atleast the ability
to sharpen the cutting edges.

You may want to consider some kid of sleeve and a helper to hold the sleeve
level (or slightly above level) while you work. If you are on the clock it
may be cheaper and faster to just remove decking as some have suggested.
Even if you have to replace some of it.