I think you have to either increase your budget, accept an older boat or leave the second couple on the dock.
My wife and I are also looking for a larger boat. One we can cruise the Great Lakes with or take out another couple for a long weekend. This calls for a boat in the 34-36 foot range. Anything less than 33 feet will not work for your intended use.
Do a simple search on yachtworld.com. Plug in 34-36 foot, 1998-2002 for age and select $30,000-$40,000 as your price range. How many boats came up?
I suspect you should look for something in the 1990-1997 age bracket, 33-35 foot and then you might start to see boats come in under $50K.
`99 Beneteau Oceanis 352, #282 WiTCHCRAFT
Sailing Lake Michigan and the Great Lakes