Please help family and rent

What I meant was you find it hard to have the conversation because it’s family yet you are ultimately willing to ( and quite rightly!) enforce the law when you have to.

I think it’s a case that you are happy to support her through a difficult time but she’s no longer experiencing that. It puts her in a situation that she could be taken advantage of her partner.

He may be very happy with his increased income and stay in the relationship regardless.

I also think you need to do some proper research on the legal aspects of creating a tenancy with him on it. It may be possible to have him as a permitted occupier only which protects you and your sister more if their relationship doesn't work out.
I'm not an expert, but if your sister hasn't been paying rent, it's possible that a tenancy (in legal terms) hasn't yet been created. The moment you accept rent there will be.
The new Renters reform bill comes into effect on 1st May and you need to look into the implications of that too. You won't be able to evict unless you want to move into the property yourself or actually sell.
Your sister and bf are CFs but this could be a minefield for you.
Just a. thought, are you sure your sister isn't accepting rent from the b/f and keeping it for herself without telling you?

This is where the saying 'when you assume you make an arse out of u and me' comes from.

You have been very very kind but now is the time to stop subsidising their lives to the tune of £35k pa. That’s a hell of a lot of money which I’m sure your sister will be grateful for when it’s pointed out.
Either full market rent or move out -now wonder they live a ‘nice life’ -you and your hard work is paying for it!

I think you are hugely overestimating the responsibility of a landlord. Landlords are not responsible for council tax (unless a house is empty) and no insurance is ‘required’. If she’s defrauding benefits (which unlikely) that’s not the landlord’s responsibility either. And as for being responsible for if she has an accident - that’s just silly.

There might be a tax implication. But only might. OP sounds perfectly competent.

YABU for presuming anything OP. You said to her that it was free for as long as she needed it. You didn't say until she moved someone in. Now you have to have a very tricky conversation with them and you'll have to before it blows up, which will take her completely by surprise.

oh dear "words to the effect" and "we presumed" There is another thread on here about mixing fam and business....basically it never ends well.

What’s your plan if she says no or argues.

By my reckoning you are approx £150,000 down on the arrangement, presumably you can afford it?

New rent changes are the perfect opportunity to open up this conversation as your looking at all your properties and reassessing them.

Dont accept £1500, it will only create bad feelings and complications with work being done and condition of the property, rent increases etc. I’d really suggest it might be time to move them on.

Sorry but it's mostly your fault, when your sister asked can she move her man in ? You should say yes but you expect to receive some money back in rent. You should have explained rent free' was until she got back on her feet, not Forever.

You didn't say anything and waited for her to offer. Shes not going to. The only way your ever going to get any contribution for rent will be by directly requesting it. Although you've left it a bit late, there's still time. Youl have to be direct and say you didn't offer a free house forever just until she got back on her feet.

You are paying her rent for her. The opportunity cost to you (of them living there free) is the commercial rent you could otherwise realise. You are gifting them this money every single month from your own income.

Does your mortgage lender know she has been living there rent free ? If not you have contravened your mortgage if you have one.
You can allow someone to live in your property rent free but without paperwork as a landlord is not good practice at all. But you are familiar with rental and know this. I am sure you would definitely not want this to turn legal. Your sister and her boyfriend of two years now might see it differently.

You are being taken for a ride.

It was very kind to help your sister out, but this is next level taking the piss. The freeloader, couldn’t even buy you lunch, and a conversation regarding rent should have taken place before he moved in. Unbelievable that he didn’t raise it. Any decent person would have.
Time to have the conversation.

Nobody is entitled to their siblings wealth. Perhaps OP worked hard for the properties she owned, or perhaps it's OP's husband that brought that asset into the marriage. Whatever the reason OP's sister has no right to indefinite free use of this proprerty.

She's lived rent free for years and is in a stable relationship with a decent earner, time to move out and find their own place. Or start paying rent.

You yourself say it’s different with family . Legally it’s not

I didn’t say that landlords don’t have obligations did I?

Are you sure there isn’t some legal requirement for your sister to at least pay a peppercorn rent to keep things above board?

Ive never been a landlord but I have a memory of discussions about letting family members live in houses they don’t own and paying no rent at all. There’s protocols to do with insurance requirements and obviously council tax, whether your sister is in receipt of benefits etc etc. if she has an accident in the house might you be held responsible? Have you had all the necessary checks to do with electricity etc and if so there’s a cost to you What happens if something integral needs replacing? There’s a leak or roof tiles fly off. Are you paying for those repairs or is she?

This is my long winded way of saying that legally it would make sense for her to become a rent paying tenant with an actual contract. It protects both of you and if that needs to be said to make sure they pay you rent then so be it.

Just tell them you need to let the house to someone else. Give them a generous amount of notice, maybe 3 - 6 months. Keep it friendly and don't feel bad, it is your property after all.