On purchasing a dSLR

I've been tossing around the idea of purchasing a DSLR for a few years now. I'm still unable to decide whether I wish to commit to this purchase.

I've sampled a few DSLRs in the past

• Canon Rebel XS - for a weekend. Didn't like it
• Sony Alpha A230 - drove San Diego to SF along PCH and took some photos.

Pros as far as I can see

• better photos
• better photos in more conditions

Cons

• more expensive than my current H300 and will take more investment in LowePro bags, lenses and stuff
• I'd have to learn how to use the thing. 
• I'd have to haul it around. I hate carrying things - especially heavy and fragile that I have to closely guard

/r/gameswap is the best thing ever

Here is a small sample of games that I've played and traded via /r/gameswap. Amazingly I've only gotten screwed once. Each trade ends up costing about $4 for USPS shipping and media mailer envelope. 

• Modern Warfare 3
• CoD Black Ops
• La Noire
• Brink
• Rage
• Crysis 2
• RDR
• Killzone 3
• Resistance 3
• Dead Rising 2