With your help I've been able to get BookCAT and Legacy 8 running, although I don't yet know how much functionality is limited.
The Strat-o-maric Baseball game still fails with a protection fault. The looks like a misplaced VC80 and MFC80 to me.
The log and the failure message are displayed below:
** Tue Jan 21 19:07:37 2014
Starting '/Users/elizabetholson/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/bin/wineloader' 'winewrapper.exe' '--workdir' '/Users/elizabetholson/Library/Application Support/CrossOver/Bottles/BB2013SETUP.EXE/drive_c/Strat-O-Matic Baseball' '--start' '--'
'/Users/elizabetholson/Library/Application Support/CrossOver/Bottles/BB2013SETUP.EXE/drive_c/Strat-O-Matic Baseball/SomBB.exe'
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0020:fixme:actctx:parse_depend_manifests Could not find dependent assembly L"Microsoft.VC80.MFC" (8.0.50727.762)
0020:err:module:import_dll Library MFC80.DLL (which is needed by L"C:\Strat-O-Matic Baseball\SkinCrafterdll.dll") not found
0020:trace:seh:raise_exception code=c0000005 flags=0 addr=0x0 ip=00000000 tid=0020
0020:trace:seh:raise_exception info[0]=00000000
0020:trace:seh:raise_exception info[1]=00000000
0020:trace:seh:raise_exception eax=00000000 ebx=006bb634 ecx=0033fd6c edx=00110064 esi=006bb588 edi=7b861460
0020:trace:seh:raise_exception ebp=006bb67c esp=0033fd74 cs=001b ds=0023 es=0023 fs=1007 gs=000f flags=00010246
0020:trace:seh:call_stack_handlers calling handler at 0x62773e code=c0000005 flags=0
0020:trace:seh:call_stack_handlers handler at 0x62773e returned 1
0020:trace:seh:call_stack_handlers calling handler at 0x60bdd0 code=c0000005 flags=0
0020:trace:seh:call_stack_handlers handler at 0x60bdd0 returned 1
0020:trace:seh:call_stack_handlers calling handler at 0x7bc859a0 code=c0000005 flags=0
wine: Unhandled page fault on read access to 0x00000000 at address 0x0 (thread 0020), starting debugger...
0020:trace:seh:start_debugger Starting debugger "winedbg --auto 31 120"
0020:trace:seh:call_stack_handlers handler at 0x7bc859a0 returned 1
Command output:
Unhandled exception: page fault on read access to 0x00000000 in 32-bit code (0x00000000).
Register dump:
CS:001b SS:0023 DS:0023 ES:0023 FS:1007 GS:000f
EIP:00000000 ESP:0033fd74 EBP:006bb67c EFLAGS:00010246( R- -- I Z- -P- )
EAX:00000000 EBX:006bb634 ECX:0033fd6c EDX:00110064
ESI:006bb588 EDI:7b861460
Stack dump:
0x0033fd74: 004260f7 00000001 b9849448 006bb588
0x0033fd84: 006bb588 0033feb0 ffffffff 006caa64
0x0033fd94: 012bca50 003c003b 0068c064 ffffffff
0x0033fda4: 006bb588 0033fdcc 006b64f0 006bb588
0x0033fdb4: 00000000 0033fe00 005f0fab 00000002
0x0033fdc4: 000f000e 005f0fab 80000001 0068c064
0200: sel=1007 base=7ffc0000 limit=00000fff 32-bit rw-
Backtrace:
=>0 0x00000000 in <wine-loader> (+0x0) (0x006bb67c)
1 0x0128d6a0 in <wine-loader> (+0x128d69f) (0x0128d6e0)
0x00000000: -- no code accessible --
Modules:
Module Address Debug info Name (36 modules)
ELF 0-82001000 Stabs <wine-loader>
PE 360000- 3d0000 Deferred sqlite
PE 3d0000- 3de000 Deferred dz_ez32
PE 400000- 76e000 Deferred sombb
PE 1140000- 117c000 Deferred stratconvert
PE 10000000-10104000 Deferred freeimage
PE 20000000-20021000 Deferred dzip32
PE 30000000-3001c000 Deferred dunzip32
PE 407a0000-407a4000 Deferred advapi32
PE 41810000-4184b000 Deferred user32
PE 41940000-41947000 Deferred gdi32
PE 41a50000-41a54000 Deferred version
PE 41ad0000-41b74000 Deferred winemac
PE 435a0000-43616000 Deferred winmm
PE 43650000-4365a000 Deferred winspool
PE 43690000-43698000 Deferred shlwapi
PE 436f0000-436f4000 Deferred rpcrt4
PE 44ba0000-44ba8000 Deferred oleaut32
PE 44cb0000-44cb8000 Deferred ole32
PE 44dc0000-44dc8000 Deferred wineps
PE 44e20000-44eb8000 Deferred comdlg32
PE 44f00000-4505d000 Deferred shell32
PE 45110000-4513f000 Deferred comctl32
PE 45210000-45233000 Deferred oledlg
PE 45240000-45244000 Deferred ws2_32
PE 453c0000-453c4000 Deferred riched32
PE 453d0000-453d4000 Deferred imm32
PE 453f0000-453f4000 Deferred msvcr80
PE 45420000-45424000 Deferred msvcrt
PE 454b0000-454b4000 Deferred msvcr100
PE 454e0000-454e4000 Deferred gdiplus
PE 45560000-45572000 Deferred oleacc
PE 45580000-45583000 Deferred msimg32
PE 7ac10000-7ac14000 Deferred riched20
PE 7b810000-7b9ad000 Deferred kernel32
PE 7bc10000-7bc14000 Deferred ntdll
Threads:
process tid prio (all id:s are in hex)
00000008 winewrapper.exe
00000009 0
0000000c services.exe
0000001c 0
0000001b 0
00000016 0
00000014 0
00000012 0
0000000e 0
0000000d 0
00000010 winedevice.exe
00000018 0
00000017 0
00000015 0
00000011 0
00000019 plugplay.exe
0000001e 0
0000001d 0
0000001a 0
0000001f (D) C:\Strat-O-Matic Baseball\SomBB.exe
00000020 0 <==
00000021 explorer.exe
00000023 0
00000022 0
Command error text:
***** Tue Jan 21 19:07:37 2014
Starting: '/Users/elizabetholson/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/bin/cxavscan' '/Users/elizabetholson/Library/Application Support/CrossOver/Bottles/BB2013SETUP.EXE/drive_c/Strat-O-Matic Baseball/SomBB.exe'
CXConfig->read(/Users/elizabetholson/Applications/CrossOver.app/Contents/SharedSupport/CrossOver/etc/CrossOver.conf)
Found no antivirus tool