I LOVE the digital homesteader description.! For me I was looking towards the same kinds of ideas as in: Oke i love to travel, but in the end I like having a place to call home, where ever in the world that me be.
I like working with clients (patients in my case), but I get annoyed how it sets boundaries in my life. As like you I love sitting on my porch, overlooking the sea and enjoying just being there.
I honestly think you could make a good life out of living on Steem. Especially where you live in the Phillipines where the cost of living is not super high this should work. Only thing you should consider is having a serious buffer for when the price drops like now, and in the end if you would not miss your hr contacts (as in talking to people every day)
Having a good home to return to is also important as traveling and experiencing life.
It might not be as expensive as first world countries but it is still expensive especially food. For an agrarian country fruits and vegetables are expensive here and often it makes more sense to just eat meat or processed food which is not healthy.
Then indeed when the prices drop like it is write now then that is another problem if I would be embracing a digital homesteader lifestyle.
Thank you for the great comment !