try something like this (ran against the data above - don't know if I can get this fond to be non-proportional, but try running against the data you showed above.
awk -F: '! /^$/{
nf=split($1, X, " ")
if (X[4] ~ /\$/)
{
printf("%s %5s %-6s %7s %4s %4s %3s %3s %3s %3s %3s %3s %5s %5s %10s %2s", X[1], X[2], X[3], X[4], X[5], X[6],
X[7], X[8], X[9], X[10], X[11], X[12], X[13], X[14], X[15], X[16] )
}
else
{
printf("%s %5s %-6s %-7s %4s %4s %3s %3s %3s %3s %3s %3s %5s %5s %10s %2s", X[1], X[2], X[3], " " , X[4], X[5], X[6],
X[7], X[8], X[9], X[10], X[11], X[12], X[13], X[14], X[15])
}
printf("%3s %3s %5s %3s %3s %3s %3s %3s\n", $2, $3, $4, $5, $6, $7, $8, $9)
}'
Not sure what you are expecting, but I got this - still see some errors to clean up.
FEB 20-98 VLY 1041 2094 8 8 8 8 8 8 NB SMITH GW - - LAPS 8 40 - - 1
JAN 7-98 VLY 1030 2064 6 3 3 4 4 3 2071 NB SMITH GW - - LAPS 6 40 - - 1
MAR 9-98 VLY $500 1024 2060 5 2 3 4 2 2 2063 1900 SMITH GW - - LAPS 8 36 - - 1
MAR 13-98 VLY $1,350 1004 2022 2 3 2 2 1 1 2022 1130 SARAMA GW - - LAPS 7 31 - - 2
MAR 27-98 VLY $675 1013 2020 4 1 1 1 1 2 2020 *1750 SMITH GW - - LAPS 8 60 - - 2
MAY 1-98 VLY $1,500 0594 1594 2 1 1 1 1 1 1594 *9500 SMITH GW - - LAPS 7 70 - - 9
MAY 9-98 HILL $2,000 0581 1570 1 6 5 4 2 1 1570 *2200 SMITH GW - - LAPS 7 60 - - 8
MAY 15-98 HILL 1003 2011 7 8 8 8 8 8 *265 SMITH GW - - LAPS 8 75 - - 9
MAY 21-98 HILL 0593 2010 7 8 8 8 8 8 9550 SMITH GW - - LAPS 9 46 - - 2
FEB 22-98 VLY $675 1013 2020 4 1 1 1 1 2 2020 *1750 SMITH GW - - LAPS 8 60 - - 3
APR 3-98 VLY $675 1001 2011 3 2 2 3 3 2 2011 *1550 SMITH GW - - LAPS 6 45 - - 5
MAR 8-99 VLY $500 1024 2060 5 2 3 4 2 2 2063 1900 SMITH GW - - LAPS 8 36 - - 10
MAR 13-99 VLY $1,350 1004 2022 2 3 2 2 1 1 2022 1130 SMITH GW - - LAPS 7 31 - - 7
AUG 25-98 RIDC 1011 2011 9 4 3< 3< 7 7 2024 820 MILLER TF - - MILE 9 69 - - 6