So clayton has the 1988 Oakland A's, who won 104 games and an AL pennant. This is a good team, make no mistake, but it's a team with some weak spots that might be exploited.
Offensively, the A's best position players are mostly 1B/OF types: Canseco, McGwire, Dave Henderson. They infield options are passable but hardly glamorous, and what's more, they're almost entirely devoid of cheap bench options. The 88s have only one position player under $1M, and even he costs $975K. On the mound, they have a fantastic closer in Dennis Eckersley, a reliable-if-unspectacular starter in Dave Stewart, and a bunch of fungible guys who all qualify more as innings eaters than anything else.
To pair with the 88s, let's serve up an earlier vintage of the same franchise: the 1958 Kansas City A's.
This wasn't a terrible team in real life--they went 73-81, which isn't winning any awards but isn't an unseemly showing. But when you look at their roster in WIS, things take a turn for the worse.
For one thing, the 58s best hitter--Bob Cerv--plays the OF, where the 88s are already strong. For another thing, they don't have a single position player who costs less than $1M, so no help for clayton in terms of finding cheap backups. And like the 88s, the 58s have only one SS on their roster, which means clayton might have to roster two $2M+ stinkers at SS if he can't find a cheap backup in the next two rounds.
On the pitching side, the 58s are just more of the same: middle-of-the-road innings eaters with problematic HR rates. Sure, there's a cheap-and-effective Duke Maas mixed in there, but it's an uninspired bunch.
Good luck clayton! I expect you'll need it.