I've had some problems hauling what I want to haul on the bike lately. This culminated when my lunch ended up falling off my rack and ending up in the dirt, plus when I stopped, my bike toppled over and landed on it's side.
There are two problems. First, my kickstand sucks. It turns out that kickstands come in two lengths. Most bikes can be accomodated with a 285mm kickstand that has little markings on the side so you can saw off part of it for a smaller bike. However, for a bike with 22" frame or larger, there are also slightly longer kickstands available. Naturally, given that only the largest or two largest frame sizes will need that extra length, my bike came with the shorter kickstand but has a frame that requires the larger kickstand. Thus, as you load it down, even without shifting the center of gravity to the left or right, it's more likely to topple.
Furthermore, if I'm bungieing a tripod to the side of the bike, it's better to use the side without any drivetrain on it, which only serves to make the bike more likely to topple.
My first thought was to buy a Pletscher dual-leg kickstand. Thing is, it's $45 and overkill. Plus, you have to lift the bike up to fully engage the kickstand. So I'm leaning towards just getting the same kickstand I've already got, just in longer form.
Now, the second problem is that I probably need to return to the subject of bike luggage. And I'm going to break this down into what I actually do with my bike.
First use case: I bike to work. I also like to bring my own lunch. We have an array of plastic "tupperware" containers for stuff. So generally I make a few huge meals over the weekend and then bring them in. So I might bring in a bowl of soup, a salad, and salad dressing. I usually just strap them to the rear rack underneath the rack webbing.
This is made harder because I've never found a bike U-Lock where I can actually squeeze the lock brackets somewhere that's not in the way. I also understand that most of those lock brackets are fairly flimsy, so I just loop the U-lock around the rack, which just gets in the way. I don't really trust cable locks and I don't really feel comfortable going out without my bike lock. So I'm stuck there.
This is where I've had the most failures. Generally, part of lunch slips through the bungee rack webbing.
I also have my laptop and various things it's nice to have around on my back. This annoys me and leaves me with a wet spot on my back. I'm eventually going to have to deal with this properly because my backpack is slowly starting to show wear.
Second use case: Going on a long recreational ride. In these cases, I want to carry more supplies than usual. Generally, this means another extra tube, a wound kit, a leatherman tool, food, a camera, and an extra layer of clothes. I keep all of the usual things I'm going to need in my trunk bag and toss the lock in there.
The only failure I've had was when my jacket slipped out through the webbing atop the trunk bag. Also, I have to stop to get anything out, which can be annoying.
Third use case: Picking stuff up. I can transport fairly large objects if I use the bungee webbing. However, I can't carry a full load of groceries, nor can I carry many objects. The more things I try to stuff on the rack trunk bag, the more likely one of them will slip through.
Fourth use case: Photography. This is a tricky one. My goal is to be able to bike to a shoot with a decent amount of hardware. This is problematic because cameras are fairly fragile items in terms of hitting the ground. If the bike topples with a pannier full of camera gear, something's going to break.
I kind of accept the idea that any solution may require some trial and error and potentially some excess bike luggage. Much in the same way that you end up with a variety of suitcases for different purposes and thus never actually use all of them at the same time. Mostly I'm trying to avoid wasting money.
I'm kind of inclined to let some problems sit for now. The photography transportation issue is a general issue that I need to solve properly. The backpack issue I'm also inclined to sit on for a while, because it's not totally annoying.
My attempt at solving the lunch situation was spending some money at Target on better plastic containers with tighter fitting lids that stack tighter.
The problem with adding to the carrying capacity of my bike is that it's going to add up quickly. I can get Arkel or Ortleib panniers, each representing one end of the design continuum, but both are fairly pricey.
Which leads me to trying to figure out if there's a cheaper way to enlarge my carrying capacity. The problem is that everything gets in everything else's way. I've got a bungee-web that hooks around the bottom of the rack. That's where pannier bags clip to, so pannier bags means no bungee... or at least using a different bungee. Some truck bags and pannier bags interfere with each others mounting points.
So, I had the thought that I'd probably benefit from buying just one inexpensive pannier bag for days when I want to drop by the grocery store on the way home or carry more things to work or home, but I'd have to figure out a better way to carry lunch.
I'm still pondering this.