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Hi my name is James I will help with your query today.
Firstly I would get the issues around deposit resolved, if you approach him about damages sought for the items referenced in your attachment, if there is a dispute over damages (eg floor damaged due to poor maintained furniture). The tenancy deposit scheme will have a disputes process where you can submit evidence should the landlord look to make deductions and that is normally a resilient process, that is concluded within a couple of months at most.
With regard to the other matters you can file a civil case (see here), you will need to provide the landlord with a copy of all evidence you rely on, so though verbally you can say to them 'everything is recorded' if they call your bluff you will have to send everything over before taking them to court.
Biggest challenge you have is proving damages, I think you may be able to claim one months rent, and have a 60% chance of winning. Alot of it comes down to why you werent able to address it during tenancy etc.
He can claim but when you dispute charges against deposit he has to show its over and above reasonable wear and tear for having a young family there for 2 years. Typically its expected a property would be redecorated every 3-4 years so claiming for repainting rooms unlikely to be accepted. The key is the landlord can claim for what ever they like but if the tenant disputes it, its down to the landlord to show beyond reasonable doubt its a valid charge.
Sorry link didnt work the government money claim advice here.
I am not clear what you mean about sending someone to court, if your mean looking at criminal charges in the case of harassment or racism then you would need to go to the police as its a criminal matter, however from experience the fact you havent reported the issue its unlikely to result in the matter progress to the landlord being charged.
The fact your dealing with small amount of money and its not really a legal issue but more of a civil dispute I wouldnt think you need a solicitor, however your better to get a quote I would think your looking at least £2000, obviously if you win the case the landlord would have to cover your legal fees (within reason).
Its based on that you dont have a great deal of evidence of addressing his behaviour (no police reports etc), no formal arrangements made, alot of it is circumstantial, you dont have a full set of recordings etc. They are many excuses the landlord could counter the claim with such as emergency repairs where they wouldnt need to give notice for entry etc.