I feel you man. Here are some things I gathered just starting out too. But before I go in to it, I just wanted to share a bit of info on software and working in a "Pro" environment.
I want to buy the monome hardware because I know it should work almost all of the time. So if it is reliability you are looking for, use hardware. That is a benefit of outboard gear. you could get into euro for about $800. buy an thonk power supply and case, a monome module, and some cheap vco's and vca's.
Nothing always works. I've set up massive templates with all my routings set so I can start working quicker. Sometimes they are not routed properly when I open that same template, sometimes live doesn't find files that are in the project folder. Sometimes you midi files or plugin settings get lost or corrupted magically (bounce everything to audio all the time...)
Most recording studios that operate as a business that need to run 7 days a week, use software that is 5 years old. Because it is at a point to where they know it always works. They rarely update to the newest version of anything. Not their OS, DAW, or even plugins themselves. Having the newest version is not worth the risk of stuff failing. To combat this I have two hard drives in my system right now with different OS's. One is Windows 7, one is Windows 8 (which I will soon upgrade to 10). But 7 will stay consistent. While I can try new things out on the newer OS, I know that 7 always works.
The other day, I tried to sync two machines in Live. I used a midi cable. Tempo, start and stop would sync, but not timeline position. I went out of my way to download the midi over wifi plugin. And it worked perfectly (using the same sync settings) and the cable did not. I even tried two different ones.
Here's the things I've learned with my monome:
Read the manual. Most the monome apps are not very user friendly at first. They have wildly different control schemes and setups. The fact that is is open source means they aren't pandering to the accessibility of the masses.
No matter how many times I double and triple checked my diode orientation, I still put 2 on backwards when building the grid.I thought I had fried the board or got a lemon, but I was just a user error. Most of the time it is. It took me posting a picture on here and somebody being like "they are backwards".
I have both a 32 bit and 64 bit version of Max 7. Some apps only work in 32 bit, like cut glove and anything that uses Karma right now. In windows, you can't switch between 32 and 64, so I have to download two versions of Max and Ableton.
In windows, you can't drag and drop files from your desktop in to Max or Live if they are running with administrator privileges.
realizing that there is usually an on button and a volume slider in the most apps that need to be assessed before most apps will make noise.
Bad usb = a very bad time.
Pay careful attention to how to save your presets and app settings. I lost a ton of very productive mlr setups until I learned how to save them correctly.
I have problems licensing max 6 with my current license too. I haven't contacted C74 about it yet, but I believe it is because you really only have a license for 7 depending on how you chose to pay. In response to that... I'm not gonna say I've never used cracked software before...
There are so many other little things I've forgotten. Most problems were solved my turning a specific setting on or off.
In the end I bought this to start learning MAX and programming. Which I have been doing very slowly. But as soon as I have made a few apps myself, I feel the investment will be worth it.
In response to @tehn and @jasonw22's discussion...
I agree that there should be a little more detail as to what apps are known to be working and problems you might face. It might be nice to even have a basic Max cheat sheet that highlights some ways you might be going wrong from the start without having to dig into the manual right away. It's more organized now with lines, but when I got my monome last year, it took me trying like 6 apps, other than sum, before one actually worked.
I like the idea of making a vst or standalone versions key apps. I was actually wondering about that. Is there a codebase that you could easily compile on to something like a rasberry pi? They use python right? I like the idea of being able to load some of the apps on to a rasberry pi and make little mini modules of software apps in a bare bones environment without needing a full on laptop. I have no idea if this would be possible or even reliable. It could be a cheaper way to have duplicates and back ups. If you little modules break or get finicky you could realistically have easy back up to switch out. You wouldn't need a backup mackbook pro for touring which costs a lot of $$$$.
I am also willing to help test and troubleshoot older apps. I see so many on youtube that I would want to try.
As far as the idea of letting go of some of the software is good. It's not giving up, but realizing what you want. If mlrv is essential to all my music performances, then I keep my laptop in a state where it works. If I want add and upgrade new gear to my software, eventually there will be a gap between what is supported by the app and what is supported by my new stuff.
I've "given up" on so many plugins when switching my OS or upgrading a DAW. When protools switched to AAX, all the rtas plugins that are no longer have support to be rewritten are gone from your set up now.
So I stay more excited about what is new to monome than what is lost. Sometimes you have to get fired from your job to move forward and get a better one.