Question for the masses:

Since 2019 I've been a 1099 Contract Employee for various (read 5-6) companies, working anything from wellsite supervision and contract petroleum engineering work. Many of the dates / locations etc overlap, making for a clean timeline on a resume next to impossible. All contracts/income etc are run through my own LLC, so in the eyes of Uncle Sam, I have worked for myself for 4 years.

As a potential hiring manager, What's the "best" method to display this on a resume?

Should I (1) list the experiences as working for 1 company (my own) form 2019 - Present with bullets for each specific role / location / time?
Or (2) list each contract out as its own entrance on the resume? Much of the experience / responsibility is the same as the roles didn't change, just the company I was contracted to

Finally - is 2 pages a kicker? (I tend to think so, but you can only add so much experience before exceeding 1 page) Leads me to opting for Option 1

Any good resume folks out there?

I recommend option one. Two pages? Not terrible.

What James and 35 said.

Option 1, and hell state in a cover letter that you've 1099'd it for a while and that has lead to concurrent jobs (that would be a positive assuming they went well and all worked out - shows you can handle and manage yourself and those work crews).

Thanks for the help!

Would you recommend a bold/italics/underline approach to call attention to the companies / work areas?

What saves the most space.

You'll need to print it out when done and have a few people review it by hand.

Don't let format get in the way of telling your story. A functional format may help you showcase alignment with your next Teams needs. Examples are available at https://www.jobscan.co/ and their optimizer is highly regarded for addressing applicant tracking systems.
Two page resumes are common for prospects with over 10 years experience. Just make sure your most compelling information is quickly accessed on page one or they won't need to look at page two.
Consider an objective (focused on their needs, line of business, and or strategic focus) to help the reader have a sense of where you might fit on their team.

The advice I got from my freshman year (and still use) was to provide the most important info the fastest. No fluff anywhere. In your case I would highlight all jobs and only give two to three bullet points. More if you have space. Touch on the most important notes like job description, leadership roles, and skills attained.