Hello all

Newbie warning, so undoubtedly some stupid questions ahead.
I've been reading the forums for a little while and am hoping to pick your (collective) brains.

I find myself in the position of having acquired myself a bloke living in Washington DC. I'm living just outside London. We've been doing the travelling back and forth thing for a while, and I'm looking for ways to make it
a) more pleasant
b) more sustainable financially for the longer term.

I recently made Bronze (year end Sep 8), and following my next 2 week trip in August will be sitting on 440TP. I realise this is minimal compared to most here, and it is being flown in World Traveller with which I suspect most of you won't be very familiar

Is Silver worth getting? Will it really make life more pleasant?
If so, any suggestions on how best to go about it?
I'll have a few days in DC when bloke is working, so the odd day trip would be possible, but apart from that I only have a couple of days spare leave.
Also, is there a particularly good/bad time to book flights? Or tricks to getting cheaper fares?

I realise these are probably impossibly vague questions, but I'd appreciate any insight, hints & tips which you may be able to share with me.

Many thanks
J