Charging leaseholder for repairs?

You need to serve a s20 Notice to both leaseholders (ie yourself too) or a s20 Opt-Out document for signing and dating.

The leases will stipulate how the Freeholder can charge for maintenance/service charge/repairs and that should be followed.

If the lease states the roof is included then it is as likewise would be repairs to a damp proof course that only affects the ground floor maisonette. Do not set a precedent of paying more than each leaseholder is obligated to pay. The ground floor leaseholder cannot refuse to pay their 50% share. But what you as freeholder could do is offer an interest free loan to be repaid quarterly/annually or at a reasonable % interest.

You say the leaseholder moved in 2 years ago, presume you mean they purchased the ground floor maisonette. If so and you knew that the roof might require work within the period noted on the TA7/LPE1 forms that should have been stated as should all major works. Was anything noted re the roof on the buyers survey?

Have you also had the correct number of quotes carried out? Usually 3. Does the roof require replacement or could be repaired? Wooden facia boards can easily be replaced by UPVC which don’t need repainting.

I think you need to go by the agreement .
First of all the state of roof affects all properties – it will effect you first but in time will affect the ground floor.

A blocked drain on the other hand wil at first only affect the ground floor but you should be ready to contribute to any such expenditure.

And of course you should expect to pay up in the case of other ground floor problems like subsidence of flooding and should be careful to make sure you have funds and/or insurance to cover such eventualities.

I would however have a conversation as early as possible about these repairs and indeed any other issues your lessee may be aware of – and work out a timetable of works and how you spread the cost.

You might wish rather than paying for the works yourself to grant him a loan to cover some of the costs of the roof work to be recovered at an affordable rate. (or when you need to attend to foundations , flooding or drains when he might be demanding you pay half! )

As far as I know, older leases gave responsibility for the roof to the upstairs flat and the foundations to the downstairs flat. More modern ones split it evenly so it doesnt all fall on one leaseholder – after all neither flat can do without a roof or foundations.
As long as you follow what the lease says, I dont see a problem – unless the other leaseholders cant pay it.

“Though I am willing to maybe contribute more than half of the costs.”

It shouldn’t be a matter of “maybe”, it should be a matter of what the lease says.