In terms of easing him into the types of problems he will face, the Bond practise books in WHSmith have different versions for different age group. So you can get one aimed at 7-8 year olds, which are the same type of problem, but easier.
I've got some "10 minute test" books for DD1, which she happily picks up and approaches as interesting puzzle books. We are not a 11+ area, but the secondary school she is going to uses NVR and VR tests to identify the most able children. DD picked up on that information during open day and got stressed about doing "scary tests". So I got them just to help her feel that there was nothing to be scared of!
I tutor (1 to 1), and am pretty shocked at what people pay for mass tutoring, computer based games with minimal teacher input, or distance learning.
I don't think I could teach as effectively on Skype, as the lessons would go too slow, and there is a lot of non verbal communication in teaching. Some children need to be refocussed onto the work quite often, and it is easy to do this with eye direction and pointing at the right part of the page. If children are writing something out (for a decoding question, for example) and they make are about to make a mistake with layout, if I am sitting beside them, I can catch it before they make a mark on the page and point to where they need to write. If they get something right from the start, it is much easier than if they repeat mistakes and have to relearn something like that. Sorry, that's a long way to give one small example.
Do check on the elevenplusexams forums to see whether Bond are the right questions for your county, and they also list local tutors.
9yrs isn't too early if OP's child is in year 5. If I wait until my dd is 10yr to help her she'll only get a few weeks before she takes the 11+ !
We're getting dd to do some of the bond books and then helping/explaining through things she doesn't understand.
For maths the same, just to find the areas she is weak on or hasn't come across before (probability, algebra, long division/multiplication, fraction, decimals) and doing extra work in those areas and then more practice papers (this is gradual btw she is only doing one paper in each area - 10 mins for verbal/nonverbal and 30 mins for maths, so less than an hour a week)
I don't know if what we are doing is right but I hope so!
The general rule is as follows: the more writing is to be done, the less productive Skype lessons are. On the age side, 9 seems to be a bit too early (from the words of our maths tutor, who gives Skype lessons as well).
If you are going to sit tests, obviously you'll need to be prepared to them.
Easing in - there are some puzzle books that have verbal reasoning type puzzles in. We were well stuck into some little ones from Smiths before we realised how similar they are! Do some for fun over breakfast together or something.
But, tbh, if he is going for competitive schools, he will need to practise the real thing under proper conditions, nearer the time, because of the speeds needed. I know, it is mad.
Has anyone tried this and was it useful? I see that Bond 11+ are offering this sort of service and I wondered if it was too distant to work well (I know how frustrating conference calls can be for instance).
Also, how does one very slowly ease a 9 year old into verbal reasoning? I don't want to go over the top, but he won't get any prep from his state primary and I don't want the idea of such a thing to be completely new to him a couple of months before a test.