You might want to check how much your insurance company charges you for public liability insurance and then compare this to the cost of BHS Gold membership where this is included. If you are already a BHS member them you may find you have been doubling up on this, so can make an easy saving.
You...
Get yourself on to the BAPSH and UK Lusitano Owners groups on Facebook and there are lots of people there who can help you.
However, there are a good number of PREs and Lusitanos already in the UK, so please don't discount this.
I would get legal advice from someone who has knowledge of agricultural land law. Depending on how long this person has been using the land it may be likely that they have created some sort of hold on the land for themselves.
Pro Tector. Very comfortable and safe. Also comes in a huge variety of colours :).
They also do a free made to measure service so you know you will get a good fit
I presume that your foal will be coming home from a Stud? If so, speak to them first and I am sure they will be able to talk you through all the options available to you.
If you speak to D&H direct, they should be able to direct you to local stockists.
My advice would be not to overcomplicate...
Try Steve Mills at Horses in Motion. He transported my boy from Lincs to Surrey last year. Reliable, reasonable cost and the horse arrived in great shape. Would definitely use him again.
If you are going to get an experienced person to take him out, why don't you go along on your bike with them? You may get some good tips on how to handle his evasions and enjoy the good bits.
I guess if he has spent so long with other horses in a riding school environment, it is a big ask of him...
Can you get someone to cycle with you instead? I bet one of your friends/family members have or can lay their hands on a bike. It might get you one step closer to your horse hacking out without the company of another and still gives you someone to talk to/for moral support.
The first ride...