Here's a better example from a past bill.
12/10: Spent $0.71 in 22 transactions. 1 mile earned for base spend, 1 mile earned for 10% bonus (rounded way up), 220 miles earned for 22 transactions.
$0.71 was forgiven as Chase doesn't bill for $1 or less.
Total of 222 miles.
Based on this I think $100 is the right crossover.
Seems like the 10% bonus is rounded up, but on a per statement basis, not a per transaction basis.
The only way to get an exact read on a per transaction basis would be to award partial points to each transaction. True Chase will round up, but it seems only on a per statement basis, so actual transactions will be closer to the partial point basis.
Thus at $25 Freedom would earn 25+10+2.5=37.5
Ink Bold would earn 25+5=30
At $95 Freedom would earn 95+10+9.5=114.5
Ink Bold would earn 95+19=114
At $99 Freedom would earn 99+10+9.9=118.9
Ink Bold would earn 99+19.8=118.8
At $100 Freedom would earn 100+10+10=120
Ink Bold would earn 100+20=120
At $101 Freedom would earn 101+10+10.1=121.1
Ink Bold would earn 101+20.2=121.2
At $200 Freedom would earn 200+10+20=230
Ink Bold would earn 200+40=240