You need to buy the best that you can afford.
After 12 years of riding, I finally upgraded from my trusty black leather jacket & custom made leather trousers, to a 2 piece Hein Gericke suit with armour, purchased from their store in Manchester, England last year.
I spent a lot of time looking for 2-piece leather suits down here, traipsing around Hamilton & Auckland several times, and being VERY disappointed in the stock on offer, ie. next to nothing.
I found a good Technics suit in Khyber Pass, where the trousers fit perfectly, but the jacket was designed for some hulking, front-rower rugby player with a bull neck, who was about 6 inches longer in the upper body than me.
The market is too small down here to warrant shops holding a lot of leather in stock and there was certainly no option for mix & match jacket/trouser sizings.
If your jacket is a good grade leather, I'd go for a back protector underneath. Upgrade your trousers if they don't fit. You didn't mention boots ... If you haven't got decent, armoured motorcycle boots yet, get some! I've had great wear & accident protection from my Alpinestars (I'm on my 3rd pair in 12 years
).
When you upgrade your helmet, I wouldn't worry about make. You need to get a helmet that fits firmly (almost uncomfortably, actually, cos the padding will shape to your head) and has the features you require, at a price you can afford.
I'd hit Motomail one weekend and have a talk to them about what sort of deals they might be willing to do you - they're great guys & gals in there. 
Waterproofing your current jacket: Snowseal is great.
True! You need to warm your jacket up (I use my oven during the winter, or outside in the sun, especially if it's black, during the summer) and apply the snowseal while the leather is warm. It will soak into the leather & virtually disappear. APPLY MORE SNOWSEAL. Keep applying it until it doesn't soak in anymore & then buff off the excess. Your leather jacket will then be virtually waterproof, in the true sense of the word.
Good luck.
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