As I understand the choices, its a choice between, off road trainers, walking shoes and walking boots. Some people like off-road trainers, I don't like them for hiking but I do like them for off-road running. Walking shoes are great but your ankle bones are not covered. I don't go for them because I like my ankles to be covered. I've only had one pair of boots that were well above the ankle, again I didn't like them because they made my lower calves sore. That's just me of course, other people I'm sure like them very much.
Then the choice is either full leather or the more modern type of boot, a mixture of leather and fabric. I've had both. In my personal experience, the full leather ones have kept my feet dry for long periods of time, whereas the leather/fabric boots I bought, leaked rather quickly. But saying that, at the moment my boots are the leather/fabric type, they haven't leaked mainly because I haven't experienced much rain when I've been wearing them. I'm still waiting to find out.
Then, of course, there is sizing to worry about. I went to Cotswold Outdoors, they did a good job and advised me, due to my narrow ankles, to always buy women's boots. Before then I used to get blisters, now that I wear woman's boots I don't get any. From my experience, you also need to try the boots on before you buy anything and it would be worth making a decision about, will you want to have to cushioning inserts in your boots or not? I always have them, on long hike days without them my heels become very sore. If you want inserts you may have to buy a half or a one size bigger boot.
From personal experience, I believe that, on balance, the leather/fabric type of boots are always (too strong a word?) a bit more comfortable 'straight from the box' than leather ones. Other people may suggest differently? I know in my case my leather boots needed a bit of time to bed in.
I hope this is helpful to you. Please remember though that this is only my personal opinion, other people might have very different views about your question and about my advice.