Figgyroll:
I realise you are securely employed - your salary probably increases by a set increment & percentage each year - but that isn't everybody - moreover a lot of families are under a lot of financial stress. Last Monday's guardian suggested several million people were literally one pay check away from losing it all.
So let's review your points from the devil's advocate point of view:
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ill fitting underwear - maybe elastic gone
Is this a single mother with several children who's handing underwear down between children, because she sincerely can't afford new nickers every year for each child? If they're clean but slipping now and then - from her perspective she may see it as a workable solution and the child will grow into them anyway.
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sandwich chucked into plastic bag along with leaky drink
all the water bottles I've bought new this year from Sainsbury's leak like mad - they were all over £5 each, so I don't think I was being cheap - they just are made in some factory somewhere where staff are paid probably next to nothing, shipped to the UK and frankly I don't think anyone (Sainsbury's included) is that concerned about the quality of the product.
Sandwich thing - She may have felt that sending it in a plastic sandwich box was not going to work because her DC would struggle to open it to get the sandwich out. Mum may have been working an early shift and forgot to tell Dad and he's just quickly put something together so that at least the child had a sandwich. (all of these scenarios have taken place at our school).
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£2 spending money. The letter was sent well before the trip and may well have been mislaid by the day so the parent/ carer may have forgotten about the spending money thing. Or the family may genuinely not be able to afford that extra £2 - especially if the trip is at the end of the month.
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Not knowing difference between river/ seaside
First of all - isn't that the point of the field trip in the first place? Why should a child who's probably never left their local area know the difference between river and seaside - and why as an educator are you saying it's the parent's responsibility to teach this. Sure in an ideal world a parent with resources will most likely have taken a child on a trip or pointed out a river (possibly crossing one on a drive) - but not everybody is in that situation.
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You can't insist that parents have rows to your convenience. Has DH spent all the money of booze that night so DC can't take the £2 for the field trip? Has DH just lost his job and they're rowing about how they're going to survive? You've no idea what is going on in their lives. Although it would be lovely for every child to live in a home where rows never occur - I think we all agree that's honestly never going to happen.
I understand your frustration - but perhaps you need to start from a place of being less concerned about your convenience and more concerned about the children you're teaching.
Could you have reminded parents about the spending money when they dropped the children off that morning?
Could you have suggested that the children went in shorts or trousers (both of which would have avoided the nicker situation one presumes)?
Could you have discussed the field trip in advance as part of class lessons to prepare them for seaside or riverside, etc...?
If you know the parent can afford £2 - why not cover the child purchasing a souvenir and then approach the parent. I personally would be very grateful - I wouldn't want my DD's to miss out on something like that if I didn't remember to send along spending money. (Especially as each trip has different instructions - and frequently the previous trip letter says PLEASE PARENTS - DO NOT SEND ANY SPENDING MONEY FOR THIS TRIP). Also can you consider including purchasing an ice cream/ souvenir as part of the field trip price - so the money is organised already.
I'm sure you're a reasonable person - and it may be that this is coming from very well-off families who should have no difficulties behaving as you expect - but consider whether both parents work and are in high powered stressful jobs? Consider whether parents have their children dress themselves in the morning and perhaps the child chose ill fitting clothes? Consider that people forget or make mistakes?