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It's possible that freeholding a two up two down isn't a money spinner for xxx and a bit of a ball ache. They might be simply waiting for you both to CE and then get out whilst taking a ground rent and doing as little work as possible.
It might be worth viewing shed guy as potentially the most hostile party here - if I were you, I would go in with him and use him for his knowledge - he will know who to employ to get the job done on both the CE and maintenance going forward - whilst at the same time watching what he is doing like a hawk. It will be a bit of effort on your part but I think you might have to and realistically it will be good value work.
And he might have the means to buy the freehold from under you.
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Wow thanks for all the info! The bit I don't get is that the freehold isn't currently up for sale. Its owned by "XXX securities ltd" so why would they sell it to just him or another company? (i.e your first option).
When you live in a leasehold property you have the right to buy the freehold (aka enfranchise), even if the current owners are not selling. As long as you can pay, you can buy. What you pay is determined by your solicitors and theirs.
When you own a freehold you can sell it at any time subject to some conditions.
I'll try to explain it a bit. There are three options here really.
The first is that you pass on it, and he can't afford to buy on his own. Fine. But if that freehold is up for sale, there's a decent chance that whoever owns it will just put it up for sale on the open market or at auction. And no-one who buys freeholds at auction has your best interests at heart. They will employ a managing agent, they will charge you for ground rent collection, they will enforce the covenants for the building, and you will pay a service charge over which you have no control unless you're prepared to learn a lot about the tribunal system. If you don't think this happens, google some of the companies which do it - Eagerstates, Assethold, Triplerose - and see what hapens to their house prices. That's your worst case.
The second best case is letting him buy on his own. In this situation, he becomes your freeholder - effectively your landlord, in law. If you want to make any alterations to the building, you need to ask his permission. If he elects to carry out major works, and your lease allows it, you need to pay him for them. If you don't, he can enact forfieture proceedings against you - you can be kicked out of your own flat. You also need to pay him for the privilege of extending your lease. And there's no standard formula for that. His lawyers will be able to demand more or less what they want, within certain limits. I had a short lease (65 years) which I extended last year; the total cost came to £31k including lawyers fees. I don't imagine he'll be able to charge you as much as that - I had to deal with marriage value which adds quite a bit on - but you're still talking significant money. And he'll certainly want to make at least some of the money he spent buying the freehold back from you or your subsequent tenants.
Now think about what happens if you go in with him. If you buy the freehold with him, you can both extend your lease for nothing - just the legal paperwork. He has the ability to do this too - you both win - because you're both co-owners. You both get equal votes in work to be done to the flat. You become co-inforcers of the lease (meaning that you can challenge the shed with the legal powers of the courts behind you!). You'll also add probably about 10% to the value of both flats, because those of us with aggressive or absent freeholders know how much of a nightmare that is. Look at 'share of freehold' flats on Zoopla and note how much nicer and more expensive they are. That's no coincidence.
If you don't trust this guy that's fine. You can insist on using your own lawyers - I'd recommend Mari Knowles or Amanda Gourlay, both excellent on these matters. But a freeholder is a position of strength. A leaseholder is a position of weakness.