Not dumb questions at all Harb. Firstly, a lot of insurance companies will still honour your No Claims history for three years after you cease to have insurance in your own name. Secondly, a number of insurers will take into account a claim free history with Motability, as they do with company car drivers leaving their schemes. It is therefore unlikely that you would need to ‘start again’ with zero no claims history if you shop around.
Unfortunately, any claims that you make whilst driving a Motability car do need to be declared, but the impact of this will depend on the nature of the claim. I had to make a claim recently but nobody was injured and no other vehicle was involved. I did some dummy quotes declaring and not declaring (to see what the impact would be) and the difference was negligible.