If the paint is cracking it is probably oil base and if its a pre-1978 home it is lead.
For sure! And you cannot just keep heaping paint on if you are getting peeling all the way down to the cypress! You will be at this eternally.
You need to bite the bullet at some point and just do this right. You will love the look.
Of course the bad news is you will have to abate the lead, at least in the US.
I know this is not the news you want to hear but antique homes do look crappy after about 400 layers of paint and given the vintage of yours you are probably at 500?
If the cypress is the real deal? Well worth restoring. And working with a power scraper (a power shaver isn't so bad) will definitely help with physical fitness. Teeth might rattle a bit though. They work great if you keep the blades sharp. You might also try one of the new infrared strippers. People at the preservation warehouse where we all collected seemed to think they worked well. I have not used one. Members of our place got to check out tools for free by reservation. The place had all kinds of things are annual dues paid for. Saved us tool rental fees. Anyhow we had power scrapers, power shavers, an infrared paint remover, etc. You can rent them all at a good tool place too though.
By the way the house exterior with cypress siding I restored got sold. New idiot owners decided they wanted it better insulated (I did all the exterior walls with foam from the inside when I had walls open and was redoing/upgrading plumbing, electrical and all). Someone told them the house had to be wrapped too. So they ripped the cypress and cedar off, dumpstered it, and put up vinyl. The hysterical preservationists are still having hissy fits! Just made me shake my head and feel rather sad. I did put a lot of work into it. Not my house though. Hope they are happy.
Nothing against a nice vinyl siding job done by pros with top end materials in the right situations by the way. But to tear of perfectly great antique wood, rather expensively refinished? When it still had 100 years or more of life in it? Just to add Tyvek? And siding they think they will never have to do anything with?