1. If you move the contract from the charity to the CIC then this is a sale of an income stream and unlikely to be one that is tax free (charity sales which are pursuant to its charitable objectives are tax exempt, the position on sale of that income stream could be different). Better the charity to subcontract the delivery to the CIC. Best to do this whilst telling your client what you are doing.
Once this contract is expired you can sign the new contract with the CIC no problem.
2. Tricky one. I would say that the grant option is better, on the basis that if the charity appears to pay expenses on behalf of the CIC those expenses would need to be for the charitable objectives. Expenses related to actually running or setting up the CIC could be argued to not be within the charitable objectives and so not allowed.
I am not an expert on this, there are others who will know more.
3. Broadly, staff will *have* to be transferred undere TUPE with all rights protected.
4. IP would have to be transferred at market value for charity purposes (I think). This may give you thorny tax issues. Might be better to licence it to the CIC.
5. Not my speciality sadly
6. Some Inspectors will, some will not. Sorry that does not help much!
Thanks Alistair I appreciate you taking the time