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DSLR for anything where I didn't mind carrying a camera bag and wanted higher quality pics or would have time to think about pictures I was taking. Mini ricoh camera for taking out cycling in back pocket, and particularly not wanting to distract people with bigger camera. Based on my experience of taking photos in India, the moment you pull out a DSLR people will want to pose for photos which makes for very different pictures. Whereas something like your Sony isn't as noticeable.
Also generally I took b&w photos on the ricoh as I wasn't keen on the colour pics unless I messed around with the raw files in photoshop afterwards.
I scratched the lens on the ricoh and now have an x100s for much the same purpose, though it's less portable and in many ways less useful as a result.Also this honestly isn't why I started replying... But this has reminded me I've got a nikon d300 and 18-200 vr lens gathering dust. If you want to make me an offer based on a bit under whatever the current ebay rate is, I should probably get rid of them before they depreciate any further.
Though am away for next two weeks, so gives you a chance to do research on whether something more suitable is available. It's not the most compact lens.
Lens is probably more important than the body. My first DSLR was a nikon d70 which now seems to go ridiculous cheap on ebay for something that'd still take really good photos. D90 seems a good choice (seems to be 100ish). Am out of touch with nikon lenses, but imagine someone will be able to make suggestions. Lenses hold value better so worth putting more money into that and less into body. Kit lenses generally ok, but if you're only spending 100ish on the body then you could get a higher quality lens.
I think it's a great idea to get a Dslr based on what you've said about the holiday. But take your Sony too. On recent holidays I took a Canon 7d plus a little ricoh gr camera and used both about equally, but for very different things.