Hacksaw my friend; I think we have all been here a few times.
This is only my opinion and not meant as criticism in any way, but the only way to fully be comfortable with what you carry is to get out there more in the field and learn the hard way. I spend a lot of time in the field, sometimes because I want to, sometimes because the Army makes me. I always carry a special note book with me EVERY time I hit the field either on my own or with the Military called my “lessons learned” note book. Every time I find a better/ easier more efficient way of doing things or an item of gear I wished I had taken or wished I left behind I write it down and then transfer it to a file on my computer when I gets home. By doing this I am 95 % comfortable with the balance between what I need to have and what is nice to have. Every single time I go out I learn something new about what works and what doesn’t with my gear. The other 5 % I have spoken of is my realization that I will never be 100% happy with all my gear all the time as every new item that gets put on the shelf in stores has the potential of replacing something that I am carrying now, making me think there is something new I need to buy and to test (I no longer fight this force, instead I accept it ) I know living in a condo downtown doesn’t allow you the same opportunities as some people to test your gear as much as you would like before getting into the field but you will most likely drive yourself crazy packing/repacking your gear until you can test it outside more. The first time I headed to the field in Alberta this time of year just after being posted here in 2000 and forgot to bring Vaseline to prevent my boot laces from freezing together and my hands from chapping is a mistake I will never make again. It is also an experience that I could never have learned until I got out there and found out how painful chapped, cracked hands are after a week in -30 weather trying to untie boot laces. Now one of my winter survival items is a small squeeze tube of Vaseline. I also learned the hard way to dump my camelbak because there is no way this time of year to prevent it from freezing. The bottom line is that the more you get out and use your gear, the easier it will become to decide what is needed or just nice to have and what to add or take from your gear to achieve that (ALMOST) perfect balance.

P.S. Although some of these primitive skills/survival skills courses appear to be a big benefit, The most valuable lessons you can learn will be from the things you experience on your own. Be it sleeping on your balcony to test a new sleep system like you did or stomping around a backyard practicing how to light a fire in the rain the best teacher you will have will be yourself. Don’t let a lot of these so called experts fool you. I just came off a 4 day survival skills course a few months ago with the Military and was embarrassed by how little the instructor actually knew. As an example, I started practicing with sparking tools by lighting my fireplace at home, and then I progressed to lighting small controlled fires in my back yard with natural tinder in all sorts of weather. Once I was comfortable with that I took it hunting and continued playing with the skills there. I didn’t need to spend big money for some self proclaimed survival expert to teach me the same thing. Don’t sell yourself short, you will be amazed at what you can learn all on your own.