Each of those 100 transactions would still be linked to the original on chain you have to break the on chain link either by swapping to Monero and back but in a different amount or by using a coinjoin transaction like Ashigaru whirlpool. Coinjoined UTXOs are not accepted for selling at any exchanges and many merchants don't take them either so going Bitcoin to Monero back to Bitcoin is your best bet as most non-KYC exchanges on trocador.app or through Cake Wallet dont flag as tainted Bitcoin. I've used Pegasus swap, exolix, fixed float and more and never recieved a tainted UTXO.
As long as you're using Tor routing on whatever Bitcoin wallet you're using you have a strong degree of unlinkabikity from your final Bitcoin UTXOs at this point.
Going to the basics here since it seems you're a little new to blockchain analysis, each Bitcoin transaction spends one or more Unspent Transaction Outputs (UTXO) and results in a recipient UTXO (The full amount you're sending to the recipient) one change UTXO (the remainder that you're recieving back as change) and the fee which goes to the block miner. On-chain each transaction you make is linked to at least the UTXO that was spent to create it. If you spend two or more UTXOs then you also link those to the same owner.
If you split a UTXO that is legally linked to you (KYC process and wallet verification exchanges require before withdrawal) into 100 and anything happens with those that would be considered illicit, say the IRS claims you owe taxes on those, you're going to be the first suspect and you'll have to basically prove your innocence that you don't own them anymore.
A coinjoin breaks this link by mixing your UTXO into basically one giant transaction with many other users UTXOs and outputs equal value UTXOs at the end making each equally likely to be owned by each input. Because there are almost certainly tainted UTXOs as at least one input, you basically taint your coinjoined UTXO with that coins history in the eyes of Chainalysis.
Swapping to Monero looks like you send the Bitcoin UTXO to an exchange's wallet (known by law enforcement) but due to Monero's untraceability (I can explain more about this if you're curious) there's no inclination as to what happened to it on chain, while you now have that value of Monero in your wallet. If the exchange has their transactions subpoened by law enforcement (happens all the time so you have to assume it's the case) then they do know that you swapped to Monero. This is why I propose buying Monero in the first place, as in the US this is a taxable event. If you're insistent on buying Bitcoin I would ensure your cost basis at time of swap is as close to 0 gains as possible compared to time of purchase to avoid tax authority scrutiny. From then literally nobody, even state intelligence, knows what you do with Monero. Now if you swap that same value of Monero back to Bitcoin in one transaction, on chain that could be guessed to be you, but if you say had $800 of Bitcoin to $799 of Monero, then like 30 min later swapped $400 of Monero to Bitcoin on one exchange then $300 on another and $99 another day there's just no way that that's linked to you with any degree of remote certainty that could stand up in court. You get away with completely KYC free Bitcoin UTXOs.
Does that answer your question? A little long winded but I hope that helps.