How do you figure it’ll get cheaper?

Honest question, how/why are you incorporated without an accountant you trust? But, if your accountant isn’t available anymore, and you’re looking for a new one… I can’t imagine Upwork is the place to find one. By “reasonable” I assume you mean cheap. When the penalty for not filing or filing incorrectly one of these forms is $10k, not sure I’d be looking for an accountant on Upwork…

I would say you’d be much better off with something like myexpattaxes.com , there are other apps like it, but I’ve been pretty happy with this one. They handle filing of foreign corporations, it costs more, but at least you know they are set up to handle most situations

Hmm, being awake from 11am-8:30pm seems ok, I guess the only issue I would have with family around is if I need to get on a call at 2am lol

Working nights but having the day available sounds pretty nice though. I’m planning on being in SEA next year, I figured I’d wake up early, like 5-6 am, have a couple hours overlap with the PST, then be able to work without interruptions and finish relatively early in the day.

Actually, I might still prefer my original plan. I’m not sure how my body would handle 4-5 hours sleep and then a 2 hour nap later

Where does Philippines say it’s ok to work remotely on a tourist visa?

AFAIK Canada is the first one to list digital nomads ok on a tourist visa, IE don’t need a work visa: https://www.canada.ca/en/immigration-refugees-citizenship/campaigns/high-skilled-workers.html

Too bad Canada is so damn expensive