Capital Gains Loss on Share against Income Tax

[anon_2011_2011]

Hi

I wonder if anyone is able to give me some advice regarding the sale of a limited company's (non-listed) shares at a loss and whether this can be offset against future income tax.

I have seen conflicting advice on general Google searches on this matter and a bit confused as to what the options are.

I joined a limited company as a director/shareholder and bought shares in 2 of the group companies virtually exactly 1 year ago.

I am looking to resign as a director and if I sale my shares in the main operating company back to the other shareholders at a loss can this be declared as a loss against income? When I purchased the shares there were effectively new shares issued to enable all directors to have an equal share holding in the business. I think this means they are Subscription shares? Are there any timing issues as I have only held the shares for 1 year?

The other company is a separately registered limited company which is related to a development project. If this project doesn't achieve the necessary permissions the shares may be effectively value less and I think they can then be declared as share with negligible value. These were purchased in the same way. The development is a land development project and I read somewhere on line that if losses are linked to land or property then a loss cannot be offset but because the loss is related to the shares in a company that was set up for the development is this a potential issue?

Are there any tax issues around a 'connected' person once I have resigned as a director?

Finally, if my future income is not sufficient to offset the loss am I restricted to only having 2 years to offset this?

Apologies for the multitude of questions but there seems to be a lot of conflicting comments on this across the web and I wanted to be sure that I didn't miss out on a potential opportunity or if there is anything I can do to improve my chance of regaining some of the loss.

I would also welcome any recommendations for completing SA tax returns around this issue as although I have previously completed my own SA, this feels beyond my knowledge.

Thank you for your time