Consider also that your 14500 may only see 500 cycles while the Eneloop will see 2100+. But if you wish to ignore this, then an Eneloop Pro 2500mAh does indeed eek our a victory over the same sized Li-ion and with the same number of available cycles.
Not really as I quoted an 800mah 14500, and there may be 850-900, even (as you mentioned) 1000mah 14500 which means MORE power than a 2500 Eneloop Pro. The big disadvantage of Eneloops is the lower voltage hampers their performance vs a 14500. It takes at LEAST 3 times the current from an Eneloop to match the same output from a 14500 which often can lead to power loss in use in higher output devices using a single cell. The only way to overcome this is to go with multiple Eneloops in series which with lower power density cannot compete with an 18650. A single 14500 probably costs around the same as 3 Eneloop Pro cells and Eneloops in series has a risk of overdischarging cell(s) in series causing damage to them while a single lithium ion has no issues.
The reason an 18650 NiMH only has 4-5000mAh is that they just aren't popular. If they were made like Eneloop at FDK, perhaps we would see something. So look at a NiMH LSD D cell with 10,000mAh, compare to Li-ion D sizes, and get back to me. Might be easier to find a C sized Li-ion for comparison. NiMH LSD C sizes have 4500mAh.
I've heard 32650 (D size?) and 26650 cells are not quite as dense as 18650s but should still have at least DOUBLE the power than the best LSD (or other nimh) cells of the same size. Nimh is nowhere near as light and nowhere near the power density that is why where we used to have nimh based cell phones and power tools (for a short time) that are now replaced by lithium ion batteries.
I've gone to 18650s over nimh on most things because I've had LSD nimh cells damaged in series in devices and having to juggle 2-4 nimh cells vs a single 18650 or multiple ones in parallel is no contest. I once entertained buying a nice 3AA LED light but after I got an 18650 light and headlamp that blows away any 3AA lights and even 4AA ones my eneloops (duracells) are mostly sitting in devices.
I've had poor luck with LSD AAAs even Eneloop varieties have either got damaged in series use or over time lost capacity and developed high enough internal resistance the LSD was no longer Low.
I don't really see Eneloops catching up nor winning against 18650s. About the only 2 things they have going for them is safety and use along with and in AA powered devices.
Li-ion is certainly good, but I think it was more amazing when it was novel in the early-mid 00's, and flashlighters from that era that got their hands on one were probably very happy. But Li-ion capacity advancement since has not been in leaps and bounds, but in small increments, and recently largely thanks to Tesla electric vehicles. I think the more recent killer advancement in battery tech goes to Eneloop... so I am to them like the flashlighters from the 00's were to Li-ion.
I see Eneloops still useful but more and more people are drifting away from them as a major power source to lithium ion 18650s and such.
The sad thing is I don't think you can hardly find them in stores even under a different label now which was a major selling point and you can no longer find single cell/channel chargers in stores for them which is a major drawback. You have to order Eneloops, decent chargers for them just like you have to do for 18650s now. I don't care for the pro's that much I haven't used but a pair of them since I have them but my transition to 18650 as my primary power source has them idling in some light somewhere.
Let's face it for Eneloops to gain market share they need a breakthrough or huge local sales support for them. All the power banks use 18650 or some other lithium power source now for a reason. I think the next advancement in lithium ion will probably be safety related.
I seriously doubt nimh tech will go anywhere as 1.2v cells are just not attractive power source now for todays electronics.
USB and lithium ion go together very well and rule the rechargeable world in most situations.