CONFUSED about USED....When is it fine or time to draw the line?

I have never been a snob when it comes to buying second hand.  In my late teens I was a great fan of all things vintage and spent many a Saturday morning rummaging around in jumble sales and charity shops looking for that elusively unique outfit.  It wasn't a financial choice, I was working at the time and earning good money but there was nothing quite as triumphant as finding a great outfit that no one else would have and that only cost me the kind of currency that jingles, rather than rustles....

My outlook altered slightly when my son was born, just after I turned 21.  As a single parent, I was determined he would never want for anything and would always have the best of what was on offer.  I physically baulked at the idea of dressing him in anything second hand or buying any of his toys in charity shops. To me (somewhat ironically, given my previous form), this was like an admission of pauperdom.  Of course the fact that his father had married someone else and had a child just six months younger than my son had quite a bearing on my attitude!

Years later I met Matt and went on to have two more children.  By the time my youngest, Olly, came along, we were struggling financially and made some major purchases on ebay to help ease the burden. There was an element of guilt that our 4 year old daughter had enjoyed everything brand new but it appeared to be quite the trend with families in similar positions to use such tools as ebay and Netmums/Mumsnet noticeboards - and, after all, what difference could it possibly make to a baby where their cot or pushchair came from so long as it adequately and safely served its purpose?

Its entirely possible to purchase something new or hardly worn (and we all know how easily kids clothes can have the shortest shelf life with the rate that they grow) from ebay and I feel completely at ease making such transactions because, its practically new stuff, right?

So, and herein lies my conundrum, since it is entirely possible to buy clothes and toys and baby equipment that is in extraordinarily good nick, for a reasonable price, where do we draw the line and buying second hand?  Should we be wracked with guilt for buying, say,  Christmas or birthday presents  this way?

My son has become quite the fan of Happyland toys, the farm, school and fire engine playsets etc.  To buy these new you are looking at a tidy sum and to create a little town out of all these figures you are looking at some serious bucks.  Then, in all probability, you will lose bits (only to find them buried in the garden or hiding in the back of the freezer) when the toy has long since been abandoned.  Therefore is it so very wrong to purchase somebody's preloved Happyland empire and still have enough in the post for some wrapping paper and a tag?!

I should add that I realise there are families who have no choice but to take that route and this is in no way a slur on their actions - my question relates to whether its worth saving all year for the ultimate new, shiny toy, or using a credit card to pay for Christmas presents (and theres a lot of us guilty of that) - or do we take a frugal attitude to present expenditure?

What do you think because this is my pre-Christmas conundrum and I genuinely don't have the answer?