Cold Storage Questions

I have “owned” a small amount of bitcoin over the past year or so on Coinbase, and have finally educated myself enough to know that I would like to increase the amount of dollars I am putting into bitcoin.

I also realize that I need to start accumulating in a way that actually gives me ownership. So, I have decided to order a hardware wallet and begin getting real serious about this.

I’ve been watching videos, reading through this sub, and reading articles on everything from the basics of bitcoin to cold storage etc. I have a few questions that I would love some input on from the community here before I dive into using my hardware wallet:

1. What is the best method for getting my bitcoin off of Coinbase and into my new wallet. I understand the basic process, but I mean should I transfer it to a different hot wallet first, then transfer to my cold wallet, or does it not really matter?

2. I plan to purchase additional bitcoin on a regular basis and would want to transfer to cold storage every couple months. I keep hearing people say to never use the same address twice, but how does this work if I want to add to my cold wallet on a regular basis? Am I able to generate a new public receiving address that is linked to my same private key each time I want to send bitcoin to my cold wallet?

3. More of a personal opinion question here; moving forward, what platform would you recommend to purchase bitcoin on every couple of weeks?

4. Lastly, any pro tips for someone just getting into self-custody and cold storage who’s pretty big on privacy?

Many more questions that I will continue to research, but I appreciate any input from the community!