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Hello, this is Jim and I am a dual-qualified lawyer (UK and Republic of Ireland) and happy to help you today.
Yes, my view is that this is a clear conflict of interest situation. The reason being, there is nothing to stop that director from arranging more works as the company will be paid a percentage fee from major works (the management company gets a percentage fee). The Articles of Association should confirm the director is acting outside of their duties. Section 175 of the Companies Act 2006 deals with conflicts of interest - the director should have declared this conflict and the leaseholders notified. The members of the freeholder company can call an EGM meeting and change the director or pass a resolution to appoint another so that there remains no further conflict.
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You can, yes - it would be a case of involving the Property Tribunal to consider your claim.
The procedure is detailed here: https://www.gov.uk/housing-tribunals
the claim would be historical if loss can be shown over the course of 6 years (the limitation period) and in addition to the current situation.