Long time lurker here coming out of the woodwork to respond to requests for pics...I love how my boy's tail looks, never even thought it weird before to clip (his tailed was clipped before I got him and I carried on doing it). He is generally fully clipped out, hogged and legs clipped as well...
My sharer (who is just starting) will contribute £60pm and do 2 days a week, but we are both very flexible so sometimes will be 1-4 days a week. She mainly wants to hack, with the occasional flatwork lesson.
Get him freezemarked so you don't worry. If you're really worried about the security of where you keep him I'd move TBH.
ETA - my boy is a coloured cob and it is a worry in certain areas, he is microchipped and freezemarked and kept in a secure area; I don't think you are over reacting.
I'm in Surrey, near Hampshire (Farnborough/Aldershot/Farnham area).
I pay £50 a month for a shared rented paddock with auto water and school at the yard next door, no other facilities.
Last time I bought small bag haylege it was about £8-£9.
I don't have transport :(
I cut the hole in mine a little bigger when he didn't really need to lose weight, now he does he has a brand new one with a tiny hole! Maybe put one on your horse with the hole cut bigger for a while until he's used to it? And feed hay and grass through the hole so he gets the idea.
I also...
Depending on where you can ride would you find listening to an ipod/MP3 (quietly, in one ear) helpful? I lost my confidence a few years ago, and this was the one thing that really helped. I was lucky as we were directly on a bridlepath, but obviously wouldn't recommend it if you have to ride...
Sorry to hi-jack but I'm looking for an XXL one, can swap for my wide or just buy second hand, otherwise will go on horse & harmony.
Apologies again to OP.