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Stefan, you just have to persevere, have faith in and enjoy what you are doing!
The association you mention is probably the Guild of Motoring artists. I am not in the guild myself although I have been asked many times. The advantage I suppose would be to have your work shown in the exhibitions they organise. As virtually all of my work is commissioned through my contacts and not for sale, I see little point as they take commission on what you sell.
I do not really know of any worthwhile competitions although there was one a few years ago organised by the late David Mills of Grand Prix Sportique which launched the career of Ferrigno.
Going freelance, be prepared for lots of set backs, you may think that sending proposals to teams will definitely bring you commissions but be prepared to be disappointed as only one in 20 or 30 may show any interest, even when you are well established. They will then take ages to decide if they want something or not and sometimes use every excuse going why they haven't paid you yet!
You will also find that occasionally you are working every hour going for little reward, around the clock sometimes, but then a commission will arrive or a deal comes off that makes all the toil worthwhile and there is no better buzz than the satisfaction of receiving a delighted positive response when you present your work to the client.
When I started, it was very much a hobby. I kept a record from the beginning of all of my works, sizes etc and where they went. I was startled a few years ago to open my old book and realise that my first 43 pictures were given away! My father was involved in racing and his friends and colleagues received freebies! It took a while for the penny to drop that I could earn from it. The payback has meant that several of those recipients became good customers of my later works.
Once you get a few commissions, hang on to those customers and hope for repeat business and remember to network with their sponsors and other team mates etc. using your artwork as a common link. For example, I did a painting for a driver who raced at Le Mans. Once the picture was finished copies were shown to his co-drivers, one of whom ordered a painting himself.
Remember too that although many folk may like your work, many others will not, it's just a matter of personal taste much akin to music for example. I have clients who do not like the loose abstract style of Dexter Brown for example, yet I have tendered for work to be told that my work is too tight, too photo realistic.
Good luck with it and keep us up to speed with what you are doing.
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