so ive been going back and forth on this for about two weeks now and i think im making it way more complicated than it needs to be. currently running a resonant dipole for 40m up about 30 feet which works fine, decent reports, no complaints really. but my neighbor two streets over has a vertical and he consistently gets better DX reports than me at least from what he says at our club meetings.

my lot is small-ish, maybe 80x120 feet, and the dipole is strung between a tree and my garage roughly NE/SW which i know isnt ideal for everything. i keep looking at verticals thinking maybe the lower angle of radiation would help me work more DX but then i read all this stuff about ground radials and now im nervous about committing to a big ground radial system. been digging through the ARRL antenna book but honestly some of that math goes over my head after a while.

anyone made this switch and actually noticed a real difference or is it one of those things where you spend a lot of money and effort and end up roughly where you started

honestly you're not overthinking it, this is legitimately one of those questions that doesnt have a clean answer. a dipole at 30 feet on 40m is pretty low in terms of wavelength — youre at like 0.22 wavelengths if i did that right — so the radiation angle is going to be pretty high, which means youre good for regional stuff and not great for long haul DX. that tracks with what you're seeing.

the thing about verticals though is that a mediocre vertical with a bad ground system will absolutely get smoked by a decent dipole. if you go that route youre committing to laying radials and the more the better up to a point. 16 radials is a common practical minimum but 32 or 64 makes a noticeable difference on receive and transmit. not trying to scare you off it just requires some real work to do right.

one thing you might try before spending anything is raising that dipole. even getting it up to 40 or 45 feet would help the radiation angle a bit. sometimes the answer is just more height on what you already have.

ran into basically this exact same thing last year. ended up putting up a vertical with about 24 radials, maybe 15-20 feet each, not perfect but decent. compared it back to back with my old dipole (roughly similar height to yours) and on 40m the vertical was noticeably better for anything over like 2000 miles but the dipole actually won on closer in contacts weirdly enough. so now i run both and just pick depending on where im trying to work, which probably isnt helpful if you're trying to simplify things but thats the honest answer from my experience.