Ad is the world's best Ad Frank, which means that like Mark Eitzel he can sometimes boil down his emotional perspective so precisely that a song is missing the easy reference points a listener might expect. If you write a wistful song and it sounds wistful, you're set. If it sounds ironically overwrought because it's about wistfulness disguised as self-deprecation disguised as overreaction ("The Only One I Knew In Jamaica Plain"), it might take a few listens to get it. Actually, I hadn't thought about just how much he has in common with Eitzel-- both are bleak, sexually ambiguous barflies with similar senses of humor. You may find this an unimpressive bit of insight given that Ad name-dropped Mark Eitzel a few albums ago, but I think he's grown into the resemblance, and it never struck me before.
The other thing which slowed down my appreciation of this record is its instrumentation, which happened to me last time too. I don't know where the occasional impulses to be REO Speedwagon come from, but I wish the band would resist them.