It's not hard to see the advantages of splitting tactical tonnage between multiple vessels, greater flexibility, the ability to police/patrol multiple arenas, to respond to multiple threats simultaneously without being hamstrung by diversionary tactics and as you point out yourself the fact that multiple ship engagements seem to favour the more numerous party.
I'm pretty sure Starfleet agrees with you. Most of their starships are small compared to the Enterprise-D. Starfleet's largest ships, by far, are the Galaxy and Nebula (respectively 28 and 21 times the volume of a Constitution!). Starfleet's next largest vessel design is the Ambassador (14x), followed by the Sovereign (12x), Akira (6.7x), New Orleans (5.1x), and Excelsior (4.1-4.6x). I'm pretty sure the New Orleans-class is a defunct design by 2368, and I don't think we've seen many Ambassador-class ships around after the Wolf 359 flashback in "Emissary".
Starfleet operates thousands of ships in the mid-2370's. Probably only three dozen of those ships are Galaxy and Nebula-class ships. Just because we're following the adventures of one exception in one series doesn't make it the rule in Starfleet.
It could even be that for Starfleet's shipbuilding capabilities, even a Galaxy-class starship is a small build. After all, the Nero-altered timeline has huge Constitution-class cruisers (15x the volume of a prime Constitution) and even more ridiculous Vengeance-class dreadnoughts (on the order of 10^2 times the volume of a prime Constitution) one century before the debut of the Galaxy in the prime timeline. Heck, even in the prime timeline there's Earth Spacedock (26000x the volume of a Constitution!!) and Starbase 74 (318000x!!!).