Maybe a little later to the party but thought I'd just give my 1p worth...
I've all 3 at home, I'm on air with some systems, AIOs with a few others and custom loops as well with my main PC..
From the air and AIO, to be honest I can't really find a difference. The air coolers I've bought recently thanks to
@freeagent have been amazing. Even at £42 when I first grabbed some, they where cheap and decent, but I've grabbed a couple not too long ago and they'd dropped nearly £15 down to £28 for the same cooler!! I've got one running on one of my i9 7980XE, a 2700X's, a 3900X, a 5800X and a 5900X. I've AIO's running on my another 3900X, a 3950X, a 5900X, a 5950X and a i7 8086k (I think its an i7??) too... The temp differences between the 3900X's are minimal, same goes for the 5900X's. The 7980XE seems to be much better with re-pasting my delidded CPU as it was hitting 70C under load, then 80C after a bios update... Since then after a re-paste for the de-lid (only some MX-2 stuff) it was down to 60C.. With temps being a little higher, I've seen it hitting 80C, it is at stock for the moment, I think standard voltage as well...
The AIO's I use are a NZXT Z63 and an EVGA 280mm model as well. The air coolers are the Thermalright coolers. I use a custom water cooled loop for my 3970X Threadripper which is on a slightly tweaked voltage, I think 1.15vcore or somewhere abouts, that has a Heatkiller nickle CPU block with a 560mm GTX rad with some 2000rpm Vadar fans I think (they might be the 3000rpm models, I'll check my project thread from my sig as I can't remember but with that under a full load today, it was hitting about 50C to 55C after 30 minutes of 100% usage for WCG... The fans are not set to maximum speeds either. I'd guestimate about 50%?
Custom loops are crazy money compared to what they used to be, I remember getting EK water blocks for £25 to £35 new, rads used to be about £80 to £100 for a triple model, pump/res combo maybe £100 to £150 at worst but now, I think some might be closer to £300... Depending on the reason for custom loops, the cost might be worth it. For myself, the overkill build needed an overkill cooling solution, so I've a loop for the CPU and a separate identical one for the GPU. I think they work together very well
But getting a little more back on point, I do wonder why I bothered with the AIOs as they aren't the most flexible so to speak and I used to think oh AIOs easier with RAM heights but most of the air coolers now have zero issues with it... I also thought that for fitting around the RAM the AIOs would be easier but with the tubes coming out the size of the pump from the X63's you do need to think about where your putting them for in the wrong place, they'll cover the first RAM slot, which isn't a blind bit of help for those with 4 DIMM slots to fill.....
So for me, £30 for a cooler, instead of £100 or more for an AIO and that it will cool it maybe a 1C better or so, I just don't see the appeal... Custom is mostly for looks, want or to help tame a 400w CPU beast...