I travel carry-on only and I bring a mirrorless camera, lenses, strap, bag as well as an iPad, kindle, etc.
Everyone's "toiletry needs" are different -, especially for women! So, to give you an example, here's what I pack: facewash, liquid meds (1 for day and 1 for night), moisturizer, tinted sunscreen, shampoo, conditioner, hair styling goop, toothpaste, lip balm (not solid), hand creme, sunscreen, and/or lotion, wrinkle release, a decongestant (liquid), a couple packs of antibiotic creme and laundry soap - it all fits in a 3-1-1 bag easily. The KEY is knowing how much you need for the time you are traveling! So, how to do this:
Take your travel bottles and fill them with all your liquids. Then use ONLY those bottles until the contents run out. Keep track of the number of days each bottle lasts.. You'll probably find that the travel bottle lasts much longer than you think - that instead of 2 oz. travel bottle of shampoo, 1 oz. will do just fine for the length of your trip. After you've figured that out, then you can tailor your containers accordingly. Viola - everything fits easily into the 3-1-1 bag!
Yes, it takes a bit of time to figure out,, but once you know the quantities, it's easy to plan for each trip. I've found that most "travel size containers" are too big for my needs so I've searched out smaller ones - 1/4 - 1 oz. seems to be about right for my needs for most trips.
As for OTC medications - I use the really small packing cube - I think it's 8 inches x 4? In it goes blister packs of Nyquil (day & Night) bandaids (various sizes), couple of gauze pads, a small roll of tape, antacid tablets, Alka seltzer, Immodium, a small compartmentalized box for Tylenol, ibuprofen, Tylenol Pm, Benedryl, and a tooth repair kit. After 20 trips, I can say that overall my "first aid/med kit" has worked very well. I view it as not having to cover me for my entire trip, but rather to "tide me over" until I can find the equivalent and I can say it has worked well. I've always been able to find what I've needed, albeit after a bit of research!
As for other medications I bring enough for the trip + 3 extra days which covers me in the- event of a delay plus I bring a copy of my prescriptions for the worst-case scenario.
Have faith, you can do it!!!!