I started my 1099 journey several years ago now. There was a time in O&G when contract gigs were all you could get. Degreed professionals had the option to work 1099 or not work. Most of those had 'plans' to pivot into W9 jobs, but most didn't. The downside, I found, was lack of benefits. However, the upside is that when I was working my white collar 1099 job "40 hours a week", I was also doing real estate, roofing, and I had another side business we were starting up. I had my own office and aside from getting my work done, I used that for my other businesses. For a 1099, they don't get to dictate my hours (unless pre-agreed). I worked weekends, at night, over lunch, whatever it took to get my assigned job done per the contract stipulations. When deadlines got tight, all of us got overtime pay. From there, I made sure my CPA and finances were up to date and the tax burden could be lessened to the point that it was a non-issue.
Eventually, that contract job died because the company went bankrupt. But, because I had been working my other jobs at the same time, i had built that customer base and simply rolled over to those. Eventually, Real Estate fell off, and roofing is where I settled. I am 100% in charge of my schedule, income, and can't be fired short of stealing from the company. While I have to cover my own insurance, I don't think I could work for W9 ever again.
Personally, I would go 1099 and work from home. Work two 1099 from home. Work three. Do what you want.
And yes, I would take a pay cut to work from home if that was my option. To be able to roll out of bed at 9:30 AM, grab your coffee and start working in your underwear without any office horse hockey and traffic is worth the loss. It is. The money you lost will be saved by not eating out at lunch or whatever.
Office jobs, with the exception of some roles, are a dying concept. It's not necessary. We have phones, zoom, email, high speed internet anywhere in the world just about. You simply don't need to be in the office for many roles.
Infinity Roofing - https://linqapp.com/jason_duke --- JasonDuke@InfinityRoofer.com --- https://infinityrooferjason.blogspot.com/