"Iv met his friends and they all think he's mister nice guy" charm is a con man's most useful tool! They need the gift of the gab to talk people into ANYTHING. The people in my branch of my family that are like this have talked people into giving them cars, houses, office space, even a diamond watch on one occasion that was the owners heirloom!
We don't take anything to do with them now but even those family members who do see them LITERALLY leave their wallets and phones at home when they do! (Phones because they have their bank cards linked on them and they've been known to clone and steal that way - yes even from family members!)
What you're dealing with is relatively low level "ordinary" cheeky fuckery in terms of con artistry but the methods are the same:
1 be charming and friendly
2 help out your target in initial stages
lend THEM money and valuables so they think they owe you - psychologists call this something like reciprocity strategy. 2nd hand car salesmen do it by initially marking cars at higher prices than they're willing to sell at so when they drop the price you THINK they're doing you a favour - but they already have the price they're not willing to go below in mind and they use this as a way to keep you above that, when they SEEM to drop the price you feel OBLIGATED to reciprocate - do them a favour in return - so you go higher than you originally intended...
3 isolate your mark from ANYONE likely to alert them to the reality of the situation.
4 if challenged undermine their self esteem by gaslighting etc so they don't feel strong enough to deal with you
5 if things get REALLY desperate and the mark looks likely to exit or worse seek help from authorities use shame, Gugly tripping or even an under the surface threat of violence to deter them.
Re Christmas, my Dd was almost 3 the first Christmas after I split from my ex and I was on the bones of my arse at this point! Missing meals so she ate etc. I managed to get her a few cheap gifts and she was delighted with them, I did some other things to make the day fun that didn't cost. It breaks my heart even now 17 years later to think of that Christmas...she barely remembers it and what she does remember is the fun stuff.
The following few years were almost as tough and to be perfectly honest we never had a "good" Christmas, but each year I'd do little things to make it fun or interesting and that's what she remembers. Even when she was older and more interested in more expensive options I found ways to spread the costs without getting into debt. One idea I had when she reached the stage of being into clothes and fashion rather than paying full price buying before Christmas I'd "Make" my own "gift certificate" for her where I'd promise her a January sales shopping trip (I'd set the budget) and this meant she got more than if I'd spent the same amount before Christmas. Other relatives cottoned on and loved the idea and so started getting her gift cards for her favourite shops that she saved to use on that jan sales day. We'd make a proper day of it getting lunch out etc (nothing fancy just chain places - but they too often have sales/offers on in the jan as everyone's skint and watching the pennies!) and a hot choc for the train home.
Is your dd into drawing/crafts? One idea I had one year that was cheap but looked impressive was I got her a set of those plastic drawers like these
www.argos.co.uk/product/7223811?istCompanyId=a74d8886-5df9-4baa-b776-166b3bf9111c&istFeedId=30f62ea9-9626-4cac-97c8-9ff3921f8558&istItemId=ipxaatipq&istBid=t&gclsrc=aw.ds&&cmpid=GS001&_$ja=tsid:59157|acid:844-913-7556|cid:9567867304|agid:99275640438|tid:pla-919550366044|crid:423233945506|nw:g|rnd:13005550266613236123|dvc:m|adp:|mt:|loc:1007340&utm_source=Google&utm_medium=cpc&utm_campaign=9567867304&utm_term=7223811&utm_content=shopping&utm_custom1=99275640438&utm_custom2=844-913-7556&gclid=Cj0KCQjw7Nj5BRCZARIsABwxDKIaTQ2Mp3tEP8_OsxXn5lF9mSy9qNkWlcRx51ueBHQmtL0fCHrbHwsaAu4CEALw_wcB
and filled the drawers with - a ream of blank printer paper from supermarket (cheapest way to buy paper), coloured card, a wallpaper sample book (I remember I'd loved using these as a kid) colouring pens,pencils and crayons, stickers, googly eyes, Pipe cleaners, fluff balls, glitter pens, glue sticks, crepe paper, old newspapers and magazines that she could butcher to her hearts content without risking the wrath of mum who hadn't read it yet 
, paper scissors, stencils, a roll of tin foil (this went down a treat! And stopped her keeping using up mine! And was one of the cheapest items!) ... you get the idea
She's almost 20 and she STILL cites this as one of her favourite presents ever! And that's even though in later years (and thanks to generous relatives) she had a wii and a Nintendo ds!
That set of drawers and it's contents lasted her ages and it was easy and cheap to top up and provided ideas for others to get her wee gifts too through the year. My sister was working in an office at the time and would bring her scrap (printed on one side no longer needed and not inappropriate or sensitive info on it) paper to draw away on and it would be proudly stored in the drawers for later use. I bet if you ask at college they might be able to help with something like this?
If you ask on here people will be MORE than happy to make suggestions there's LOADS you can do to make Christmas cheap but heaps of fun!