The best antenna recommended so far is a directional DB-411 which is rated 2dB more gain than your current antenna. That would provide about zero benefit and may loose performance in directions other than where its pointed. There is the big DB-420 or a Commander Technologies Super Stationmaster, about the largest highest gain UHF omni's available at 10dBd but they are only rated about 3dB more than your current antenna and 3dB will not fix your problem.I have to revise this answer. While I did manage to pull off a conversation from a portable at one point at around 10 miles form the repeater, that was making the call from an open area with a clear line of sight (mostly).
Under typical circumstances, these radios are used 4 miles out, at the most. Mostly are within half a mile. The remote buildings where I encounter the issues described in the original post are around 3-4 miles out. I went to one of these problematic locations myself, with a co-worker to conduct some testing (actually to do some work, and we took a pair of radios). We had success about 80-90% of the time, but occassionally no audio came through. This was in a campus area with some 2-story buildings constructed with concrete walls. Whenever there was a problem, the caller was indoors and on the first floor. This doesn't mean all calls failed from indoors on the first floor.
Anyways, really the issue at hand is to be able to make the radios hit the repeater antenna better in order to achieve a (close to) 100% success rate.
Don't really want to install another repeater at this remote site, and rely on the Internet to connect to the main site. That's overkill. Bigger stubby antennas on the portables? Or the suggested Commscope antenna at the repeater site?
Someone asked earlier if the problematic buildings are in all direction or are more in a certain direction. They are more or less in a certain direction covered by no more than a 30degree field of view.
I'm sticking with a minimum of 10dB more omni antenna gain than you have now to address the problem and that doesn't exist. Anything less than that will be lots of $$ spent for zero or barely noticeable improvement and will not provide reliable comms in the areas that don't work now. There are better antennas for handhelds but improvements will be a dB or two at most and will not even begin to fix the problem even with an upgraded repeater antenna. You need to look elsewhere for a solution.
If you were local to me (So Cal) I could loan you a 10dBd omni to temporarily replace your existing antenna to show that will not fix the problem. Unfortunately the antenna is too big to ship for any reasonable rate.