Hi,
Sorry I meant to respond sooner, but it is the holidays and I was on a trip. It sounds like you made great progress! In terms of getting set up to develop INDI or KStars code on a Mac computer, I developed a repo with scripts and instructions to get it all set up.
github.com/rlancaste/kstars-on-osx-craft Hopefully this will help you. It sounds like you are just interested in editing INDI though, not KStars as well? My script builds everything from scratch and then optionally prepares a DMG for distributing it all and optionally sets up a development environment for editing the code. That might be overkill for what you are trying to do right now. I might want to make an option that doesn't require building everything, so that someone can get set up to just try a quick change like you wanted to do.
In terms of the first issue you ran into, I would say your main problem was having the driver find the dylibs as you identified. When a driver gets built, it has to link to the dylibs and when it runs, it has to find them based on that link. Your solution was to "export LD_LIBRARY_PATH=/Applications/KStars.app/Contents/Frameworks". You did that before building INDI I assume? That will work as long as you don't move KStars and as long as all the libraries that you need are present in that frameworks folder.
The solution that I use in the distributed INDI drivers in the DMG is to define the libraries' ID's and links as an RPATH and then at runtime, they get the RPATH so they can find the libraries. This does require a couple of extra steps however, so might not be desirable for your application.
Do you have homebrew or craft installed on your computer? Either one of these could be used to get set up to edit INDI code without any dylib issues. Then when you built the software, it would point to the libraries in the homebrew or the craft directory respectively. This is the way I typically will edit INDI code, using either homebrew or craft.
But your solution does give me an idea, for folks who want to just edit something quick in INDI, it might be nice to have a version of the script that would let you use the already existing frameworks instead of building everything from scratch. Let me think about that.
In terms of the second issue, the uint issue you ran into. I ran into the same problem the other day when building the KStars 3.3.9 DMG. Apparently somebody made an INDI change that OS X didn't like. I addressed this as soon as I found it, but I think that was before you ran into the issue. It should be fine now.
As for the real issues you are looking into, the timeout and Serial to USB adapter, it sounds like you have made some great progress. For the Serial to USB adapter, often times you have to install some driver from the manufacturer, you said you did this from the Best Buy website for the Mac driver? I would recommend going to the manufacturer's website instead. Also, maybe try the Serial to USB adapter with another device to test it?
Thanks,
Rob