When I travel I ship my gear overnight to my hotel on the day I leave. I always have it by 10AM the next day with no worries about theft, hand inspections, x-rayed film and all of the other problems associated with traveling with bulky expensive gear. Yes, it is a little pricy but just for the ease and peace of mind I find it worth it.
You have a whole lot more faith in the shipping firms (e.g., UPS, FedEx, etc.) than I do. Items can be delayed and/or lost. It happens all the time with them. And even when it is safely delivered to its destination, maybe it will get stolen or lost by the hotel, or whatever.
On my overseas vacations I normally carry 3 bodies, maybe 5 or 6 lenses, flash, batteries and charging equipment. All my stuff (except tripod which goes in checked luggage) is squeezed into a 22" rolling backpack, which meets the size requirements of all airlines. The only places where there is a problem is on the small so-called regional jets. The rolling backpack has a smaller zip-off daypack which easily fits under any seat. That and the photovest I always travel with has, so far, accomodated all my stuff when the larger bag has to be checked.
The biggest issue is normally weight which can easily approach 30 lbs or even more. So far I haven't had the misfortune to fly British Air, which I understand has a rigid policy of unflexibility regarding its 14 lbs carryon weight limit (unless you are in business class). Some others have a low (about 18-20 lbs) weight limit but tend (apparently) not to enforce it. Also, if you are wearing it (photo vest) then it does not count against your carryon limit).
Hopefully, if I run into a British Air problem they will accomodate me given the cost of the equipment (for example, at worst case put the equipment securely with the crew's luggage). If not, then they can delay the plane to remove my luggage while I go in search of another airline.
My traveling companion has also been used as a mule on occasion for bits and pieces of my equipment that just won't fit in my rolling backpack or vest.
I packed my Monopod in my carry-on and for the first time the bag had to be searched. A monopod looks like a weapon, so better to strap it to the outside of the case.. Might make it easier