Help with my gear? Traveller, not hiker…

[Steven Diogenes]

Here's my gear list. I'd love some advice! Keep in mind it's for long-term traveling, not hiking, which means carrying more comfort and miscellaneous items. I periodically throw out everything I haven't/won't use so mostly I'm looking for ideas on how to modify/combine/replace/etc. rather than dropping objects. For ex., I'm going to ditch my nalgene and use a Smartwater 1L bottle (replacing it often). Also, I cut down a lot of clothing so I'd like to replace my OR compression sack with a cuben stuff sack. … but yea, this is my life on my back, not just a short hike. That's why I have 2 books, instruments, recorder, sage, etc. but I'm definitely open to ditching stuff. 

I only have access to a bathroom scale so weights are really approximate… as accurate as I could get. (besides the manufacturer specs)

Anyway, I welcome all suggestions or challenges!

SMD Swift w hip belts 1 lb 3
Marmot Arroyo 1 lb 11 oz
Thermarest RidgeRest short 9oz
Tenor Ukulele 1 lb 6.4 oz

misc

2 books
Microfiber small towel
Space bag (the 5L plastic bag with twist nozzle inside box wine, great for showers or water)
2 trash bags
Gloves
Sage bundle (I'm going to cut this down 3/4)
Foot powder (7oz when full)
Sew kit (thread, bag of patches, embroidery floss, piece of aida cross-stitch cloth, needles in small altoids tin, thimble)
Med kit (2 hand warmers, 9 condoms, staph antibiotics, squeezed out antibiotic tube, 8 Tylenol, 6 dayquil, 6 lg bandaids, 4 small, 1 gauze, 8 claritin)
Rope
~4lbs

2oz hand sanitizer
bic lighter
headlamp
fat sharpie
p38 can opener
small piece of deodorant in plastic
4in of duct tape
travel toothbrush
voice recorder with 1 AAA
mini caribiner- I don't know why I have this but it seems handy?
zip tie
chapstick
paintmarker
harmonica
floss
hairtie
small toothpaste
safety pin 
4 geared tuners 
fishing kit (6 hooks, 3 lures, some line, bobber, one jighead, swivel)
~1 lb?

clothes in compression sack (couple pairs of socks, balaclava, beanie, pants, light shorts, three boxers, bandana, arcteryx atom [found it!], jacket, sweater, tshirt, flannel shirt)
~5 lbs.

I'm shooting to replace my 1lb 11oz Arroyo with a Zpacks 40 at 12.3oz, and get the MLD eVent Soul bivy at 13oz, and the Hexamid Solo Plus with everything plus pole at 20.7 oz. (plus so I have extra comfort space and less rain worry)

Why both a full tent and waterproof bivy? 

A closed tent provides the comfort of a private enclosed space and adds that 'feel' of safety when covert camping in what could be sketchy areas. Whether that means animals like skunks or other humans. Also, my morale suffers a lot when I have to think about rain while sleeping.

The bivy is good for covert rain camping, inside cities (behind bushes, on roofs), in train yards waiting to catch a freight train when you can't risk being seen, in super-buggy areas like Louisiana summers, etc. Rain is tough on the road.

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