Bitcoin for Beginners

Hey all, having some trouble getting conclusive answers on a couple baseline questions. I feel that casual conversation will get them answered.

Background: Long familiarity with crypto, in early 2010’s a close friend used routinely for “trading” purposes and i even presented to my college class in 2012 outlining Blockchain/BTC. If i would have put $1 in at that time I would been up about 200,000%…I had money to play but was too stupid

Well, I am looking for some investment opportunity now although I understand I’m late to the party but I’m ready to party.

Questions:

1. Is it worth it to attempt anonymity for investment purposes even with the increased regulatory interest and potential visibility? I have an unused cold wallet on-hand

2. Am I still able to use an exchange (anonymously) to facilitate the transaction and send directly to my cold wallet? I don’t think I would want to initiate the transaction, move to hot wallet and then move to cold wallet.

3. After having coins on cold wallet, is the most efficient withdrawal taking that device to an ATM and converting specified amount to cash?

I also live in a highly regulatory state that requires a BitLicense really narrowing down the allowed exchanges.

Thanks,

OB