Kyle -- I will give you couple of specifics, both based on experience trying to help others:
1) Automatic resizing. Ppl try to upload, wait...wait...wait... forever. Eventually they give up.
2) Drag&Drop. Pic has to be dropped inside the box --which is fair-- , but they drop it somewhere on the boundary and to quote someone "whole thing blows up" (Browser shows pic as separate page because upload script didn't kick in, but people don't understand this)
End result in both cases: People conclude CT is waste of time and go to Facebook because they can't screw it up regardless what they do.
(inline drag&drop sounds good & I'd use it myself, but I'm afraid it could also backfire for same reason some have problems with current drag&drop upload, see above)
There are two sides to a resizer, what you're describing sounds more like despite what limits or lack there of we put on attachments if you try to push too much data to the site at one time it will time out. I can try to get bandwidth boosted but that only gets you so far if you're using high res photos. Having something on site that shrinks them would also suffer that same problem. The site has an auto resizer that keeps things from breaking formatting.
Re the theoretical Drag and Drop 2.0 the boundaries are a lot clearer in the posting box than the current drag area which should help with that.
I promise to return to CT when this drag and drop thingy(with a caption/description immediately below the pic) gets to where it needs to be as I have about 35 trip reports on backlog. Until then I'm outta' here
If I can get the new version approved and built then a caption would just have to be typed in under your photo placement
Automatic sizing would help me a lot with posting TR's as all my pictures are always to big to post even my crappy cell phone pictures.
Even cellphones now are taking 5 meg photos at 1080p res
Kyle: Read the above. Read it couple of times. The person that wrote this is mountaineer that goes places 99.9% of us can only dream about. He is willing to contribute to community, but you have chased him away. I know at least 10 more examples like this on Rockies side.
Basic problem you have is not (just) UI or "how to write reports". You have more fundamental issue of total disconnect with the community. End result? Except for couple of us that are stubborn & will stick to the bitter end, CT is pretty much a ghost town.
Which disconnect, time between response? That's unfortunately due to our entire network being pushed to a new server system and getting SSL upgrades leading to a massive resource cap. Or do you mean because I'm not nor are any of my team active members of the hiking community? Because honestly if that's the case I'll gladly go out and post my own trip reports.