It does look to be quite complicated there, as I see you have to file self-employment taxes in addition to your primary tax return, and do the deductions dance. I think being a sole proprietor is fairly complicated just about everywhere - I hired an accountant, and pay him quarterly to keep me in line here in Portugal. Happily, in this tiny economy, that costs me around 70$ per quarter! One of the issues with freelancing platforms is that you are often paid only by a username, so don't have the employer's details to file. A substantial number of my freelance competitors on Fiverr are based in the US, so it must be possible!
I don't know that it is any different from having one's own owner-operator business if those are the things required. I paid self employment taxes which were no big deal to do, and filing a quarterly payment is easy too because you simply base it on what you earned last year, and then pay more or get some back according to what you made this year.
to me, being a freelance/contract person sounds easier to manage with regard to taxes because if the employer pays you over a certain amount in the year, they will issue you the form you need to file that income. Otherwise, you need to keep accurate records of everything you were paid. It may, if you are like me and not good with numbers, be wise to hire someone to do your taxes each year, and that person will figure out the deductions for you and tell you what to do next year to make it easier.
If you are freelance writing, you won't have much of anything to deduct in any case, unless you dedicate one room of your house to being solely your office for that purpose, and then you can deduct that percentage of your house's payment. You can deduct your internet cost and any repairs to your computer. Maybe travel time, but only if it is between one employer and another, not from your house.
If you are going to someone's place of work or house to work then you really don't have anything you can deduct that will add up to enough to make it worthwhile to keep track because the standard deduction will be higher anyway.
I don't think it's hard to set yourself up to be a freelance employee. Especially if you already have the contacts.
What it does take is some degree of energy, especially in getting the contacts if you don't have them.
If a person has very low energy then it will be hard set up and to maintain, possibly. But I think those things are harder than the taxes..