My first new leather gear will be arriving maybe tomorrow from NewEnough. com. Got the Power Trip Vintage jacket and chaps (cream and black) for less than $200. (The chaps I'll dye black.) I'm going to have pockets sewn to the inside of the jacket and chaps for TPro armor inserts ($195 at Johnson Leathers in SF). Sure, I'm probably spending too much on the protective parts. But I figure I can reuse the CE armor on any other leather jacket or pants I buy later. And I've got lots of Patagonia ExtremeWear thermals for riding during the cold winter months and a decent wool balaclava for my head and neck. Since I'm not planning to do any freeway driving until I've had at least a good year's worth of regular street and country road riding around my home, I think the girlie 1.2 mm leather will protect me fine should I fall and slide. in a year's time, maybe I'll have lost enough fat to get some really nice two- or one-piece custom-made 1.4 mm leathers that'll protect me should I fall. By then, I hope to have graduated to a bigger (and possibly new) bike.

I can see I'm hella late to this conversation - but, as someone who is lacking meat on the top (no problem in the rear) I tend to get cold, bone cold and it's hard to shake except with a hot bevvie. I recommend layers (surprise) for the 'I get hot too' part. if I'm out for a weekender, I like a tee base, followed by a marino wool turtle neck (the light gauge kind) followed by my padded leather. the t-neck covers the extra bits where the wind likes to go (down my neck and into the itty bitty openings here and there)
other than that, I concur on the taking your time part - not much more sucky than spending money and not having it be right.

like my amigo likes to say about buying a wetsuit (lots of choices) you'll know its right when it just feels right.
and you dont really want to take it off.