it depends on how you like to travel and what you need it for. if you like to drink under bridges and ride trains, i can't really justify it unless you have some extreme need for it. if you're like myself on the other hand, someone that has a website to run, it makes perfect sense. the key really is to try and judge your situation and the people you're with and not flash that kind of stuff around if you don't absolutely trust them.
for a while i was carrying my video editing laptop, and a canon t3i with a super expensive lens. what i was documenting was great, but i didn't pull it out very often due to being paranoid about people wanting to jack it, but more so it became a drag because i was constantly afraid of breaking it. since it was so expensive and i knew if i broke it i couldn't afford to replace it, so it became a constant nagging on my mind that after a while just wasn't worth it, so i sold the camera (and this week i sold the laptop, but it served me well for 3 years and i didn't have to worry about it all that much).
i've most recently decided to move to using gopro cameras and maybe a mirrorless camera (haven't bought that yet, it's expensive) which would save a ton on weight (something i sorely need) and the mirrorless camera would be about the same size as a point and shoot but with dslr quality pictures. i'm also going to move to a windows surface pro tablet for video editing.
but i'm getting off track here. basically it's a balance of what you need the item for, versus it's weight and if you're comfortable taking the hit when it breaks (or gets stolen). i (like you) take really good care of my shit, so i've never had anything break (or get stolen), even when train hopping, but i still go out just assuming something is going to break, because eventually it will.
so... how much do you like that samsung tablet? would you use it enough to justify it? are you okay with it getting broken? keep in mind you can get a very nice nexus 7 tablet for around $150 bucks if you need a replacement.
also, people used to talk a lot of shit on train hoppers that had even a simple flip cell phone (until i showed them i could trace cars from the yard, ha) but now every gutter punk has one, so having tech gear on you isn't nearly as big of a deal as it used to be, as long as it's not outrageously expensive/ridiculous.
anyways, hope that helps.