We live in a Leasehold flat, which is currently on the market. We've had any number of issues, some our fault, some our (crappie, nonexistent) freeholders.
Our flat is what could be described as a maisonette. It's an Edwardian purpose built property. From the outside it looks like a terrace house with 2 front doors, if that makes sense. So the freeholder owns the freehold to our flat and that of upstairs.
We moved in in 1995. At the time, you could do shared ownership on the open market ie you didn't have to go for an estate, you found a property and approached the HA about buying a share. So we went in with a HA, meaning the freeholders were the original freeholder plus the HA.
When we moved in the lease was just under 99 years and the solicitor advised us to lengthen it ASAP. Tbh we were just so happy to be in (in awful council flat before) we didn't really listen to that.
For 5 years we got a demand each year for ground rent which was paid. Then the demands stopped. The upstairs neighbour went to the freeholders address to find out he'd died and we then had no idea who the leaseholder was as noone approached us.
In 2011 my mum died and I inherited some money, which I used to buy out the HA and clear the mortgage. During this process, the freeholders were located, who demanded the back rent but the solicitor reminded them that (a) they were supposed to approach us annually with a formal request which they hadnt; (b) we didn't know who they were for years and (c) legally we were only liable for 6 years. The lease was sorted out showing we were now the leaseholders (ie not us and the HA together as it was initially). However, we never heard from them again.
So last year we decided we wanted to move. By this stage, we had not been approached directly for ground rent in any shape or form, bar an indirect request via our solicitors in 2011. By this stage (and this was our fault) the lease now had less than 80 years on it. We took legal advice and basically we had no option but to increase the lease if we wanted any chance of selling, because it is practically impossible to get a mortgage with than 80 years. So we applied to increase the lease, which cost £55k plus legal to increase by another 99 years. Fortunately we had a second property (holiday let) which we sold to release equity. So now our lease is ok for us to sell but it's been a logistical and financial nightmare.
Would I go for another leasehold? No, not if I could avoid it, unless it was a share of freehold or like our holiday let was a 999 year lease, which do happen. Fortunately we moving out of London and are looking for a house making it easier. Flats are often Leasehold properties.
During our time here we've replaced the windows and boiler and tbh it didn't even occur to us to ask the freeholder! With the amount of contact we've had from them that's hardly surprising! They haven't even asked us for ground rent since the Millennium!
We've had a civil relationship with the upstairs neighbour who has always been the same regarding communal areas, roof, drainage etc and have an informal agreement that up to about £500 we cover any repairs to ground/underground works and he does the same to the roof/guttering. Anything more we go halves. We've never involved the freeholders. Luckily our agreement has worked for us.
We did consider asking the upstairs neighbour if he would consider a share of freehold but he spends long periods away and we couldn't pin him down and needed to do something with the lease asap as the shorter it is, the more expensive it gets especially once it gets under 80 years.