hi kutil
my dd is just 14 months and i kept her bf and dairy free till about 10 months.
then i gradually started her on yoghurts (big hit!) and whole milk on her cereal, in cooking etc. she'd been on rice milk previously.
since she turned one i have persevered with introducing a milk drink. this is partly because i am "encouraging" her to self wean so she is only having 2 maybe 3 bf per day these days. and tbh, that's less food than comfort!
anways, i struggled with a sippy cup as she'd never had a bottle and had no concept of tipping the cup! she has had water from a doidy since 4 months but that was just getting too time consuming!
she's had a straw closed cup thingy for water since September and I have now got a 2nd insulated one for her milk.
I give her 2/3 whole milk warmed up then cooled with 1/3 semi-skim. she sits on my knee and guzzles it then she goes for her morning nap.
we're still trying to get her to have regular afternoon milk. i have found an early lunch (11:30am) makes her want some milk about 3:30ish. She has her dinner at 5pm and is bf to sleep at 7pm.
I give her morning milk about an hour after her breakfast and it really sets her up for a nice sleep.
also, my mother makes dd a rice pudding every week and she now has lots of yoghurt and cheese etc.
don't forget, if it's calcium content you're after then broccoli and sweet potatoe are good sources.
if it's fat then mash with lashings of butter and whole milk is great. bread and butter pudding with the same might be good. pasta sauces with lovely cheese and spinach or cheese and salmon are popular here too.
HTH and good luck! My tip would be try a variety of vessels and persevere and maybe mix whole/semi and skim to see what your LO prefers.