Subjective upgrades

Before diving into my topic, let me update you on my play for the last week or so, which hasn't been much. I actually dusted off Sakuran (my rogue) for the first time in close to a month to run some quests with a RL friend of mine who's finally caught up to me in level. Playing her after focusing on my tankadin is very odd. I feel very vulnerable, which is odd because Sak's build is deep subtlety (aka, lots of survival tricks), but at the same time I forget how much damage she can deal. I'd read that playing a Paladin involved casting a few seals/judgments and then leaving the room... It's a bit of an exaggeration, but there is truth behind that statement. Sak on the other hand is much more involved to play, and I have to be much more careful with her. I think I forgot that I have vanish and prep, ended up making visits to the GY that simply shouldn't have been. L2P, I know...

So, I had earlier found Tim's Trusty Helmet off a quest in Zangarmarsh and, looks aside, was pleased with it. After clearing a few more early quests in Zangarmarsh, I had the opportunity to grab Scout's Hood. For those who are too lazy to click the links, Tim's Trusty Helmet is probably a much better items, but Scout's Hood has three sockets (one per color). I found myself is a somewhat new position, not knowing what was a better item. I suppose I could have cheated and looked on wowhead.com to find that Tim's Trusty Helmet has a higher item level, but I haven't decided how heavily to weight the presence of sockets. Before socketing anything Scout's Hood is sitting at -5 AGI, -22 STA, -22 AP, and +12 Hit. The socket bonus is +4 AGI, so I only needed to make up 1 point there, the rest of the stats would be a bit more difficult. Looking at the vendor gems was not encouraging. I could pick up +6 STA of a blue, +4 AGI of a red, and +4 hit or crit off a yellow. Not bad, but not good. I then decided to give my trusty neighborhood Auction House a visit.

Now, as I'm sure you all know, searching for gems in the AH is next to impossible. No way to only look at gems without an addon, and to my knowledge, no way to view by gem slot. So, I resorted to wowhead.com which offered a very robust gem search. I ended up +3 AGI/Hit yellow gem, +6 AGI red gem, and +3 AGI/+4 STA purple gem. This brought the difference between the items to +11 AGI, -18 STA, -22 AP, +15 hit. So it's 180 HP and 11 AP vs. +15 hit and some crit (don't have the calculation infront of me). Pretty close, but what ultimately made the decision for me is that Scout's Hood hands down looks cooler. While Tim's Trusty Helmet has some decent stats, I actually had to turn off my helmet display as it was so ugly... I'm not normally one who cares what the gear looks like, but Tim's Trusty Helmet looks kinda like an old early 1900's football helmet...

So, this leads me to ask the question: How long should socketable items 'last'. In my example above I started with an item of lower item level, and with the addition of ~8g of gems made it superior (IMHO) to the item I had. Down the line as my lazy butt levels my main I'm sure I'll run into a head piece that is clearly superior to what I have. In this scenario should I 1) take the item and drop what I have, or 2) buy better/more expensive gems to make the item I have 'better'. The choice is easier if said item is also socketable, but it is certainly a new dynamic.