I am hoping there is a few tax lawyers or at least tax informed peops out there in Mastadon land.
I have a unique tax puzzle/situation
Alaska resident, stationed in Virginia. Active Duty Military. retire in a few months, which in itself has a lot of tax implications I am not used to.
everything is set up to go to school using my MGIB. as long as I go to school full time I remain an Alaskan resident. I get to keep my vehicles registered in Alaska, and dont pay Virginia taxes. i can make a little extra income with a fed program, tax free but limited to 20 hours a week at Virginia min wage. first couple months and first year out is anticipated to be the most difficult financially, very much on my mind. I suspect I'm not calculating a lot things that will have inpacts.
Problem set 1 - if i work, or maybe even think about working, Virginia forces me to change residency, pay Virginia taxes on my military pension, and switch my vehicles over (which may or may not include use tax). it also means i cant get unemployment as I am not a Virginia resident, and wont be in Alaska.
Problem set 2 - I have a CDL i got through the military. a good deal i thought, so i did what was needed to submit everything, took my written tests...kinda been a pain honestly, real id was a nightmare. Virginia has some grey area stuff and I'm not so sure that Virginia wont make me switch it over even with full time school. there was some vague text in the law when i was looking into it. didn't get warm fuzzy answer that was solidly yes or no. part 2 of this is I was intending to go home to Alaska and work during the summers while in school. those jobs require an Alaska drivers license or CDL. if Virginia switches it over ill have to switch back and forth through out the year which is a pain. possibly dangerous as i wont have the stability or backing of the military/laws with that aspect so I'm a bit transitory. my home of record wont be usable anymore, family hasn't lived there in decades. wont have enough history in Virginia. May get stuck without anything switching license back and forth.
Problem set 3 - here is the 2020-2022 issue. remote work has become more prevalent. in theory if i work remotely i would pay taxes based on either my home state of Alaska, or the state the company is in. so technically i can get around some of these issues. i keep finding the little nagging voice in my mind that states simply haven't dealt with the problem enough yet and suspect Virginia may come after me later.
Really just looking for advice on how to not get a surprise bill for my left leg, lifetimes worth of wages or future of spring in surprise back taxes, while also not trying to lose my residency or get trapped in no win scenario. hints/tricks on setting this stuff up. i have seen things about several of these issues, but not combined like this. the first year of school/military separation is going to be rough, so i wont have a lot of leeway for a bunch of surprises. the remote work thing really twits things up even more but maybe a decent solution for part time work. I fear ill lose my mind if I don't do anything when not at school.
@Alaskanviking mm part 3: as pertaining to the remote working dynamics and options, and this is slightly connected to part 1. Also an important question is, do you maintain a residence in Alaska? If so, that gives you options:
1) Remotely working should be ok, however you must use an Alaskan address for residence on your W-2 application for employment.
2) More challenging, and yet way more flexible, operate as a "sole proprietorship", or go ahead and incorporate in Alaska. Both of those require you to handle your own taxes personally.
2.a) Have another company contract hire your sole proprietorship or company.
2.b) Any expenses related to business allow you to write off certain amounts of your taxes. This is typically far less, however you're responsible for paying FICA and Medicare manually.
2.c) Gives you another anchor in Alaska, I believe there's incentives in not just residing there, but doing business too.
I'm pretty sure the key is keeping a primary residence address there that is associated with your identification. I know times are hard, but also remember, taxes are a good thing. If you're main goal is reducing overheads and maximizing income. Nothing beats entrepreneurship, and investing returns.
i think you may have thrown another monkeywrench into the cogs for me. didn't think about the residence address in Alaska, or at least not in that way
Answer is yes & no....
Active duty military for another 4 months. so I have my home of record in Alaska, which is my residence address at the moment. my mailing address is in Virginia where I'm stationed. the address where i live is considered both my residence address and physical address. but they get intermingled and confused a lot. home of record is a legal thing, perk of being military, lets me keep my state residency while i am in.
as long as i go to school full time 12 credits I similarly get to keep my Alaska residency. i haven't dealt with this aspect and worried about it now that you said something. some of it is protected by law, but essentially i lose my home of record address, which is my sole link up there. that is ok for now as long as I don't mess with my drivers license. essentially I will no longer have anything to really prove my "residence address" anymore. vehicle titles and voter card maybe. will need to look what is on my other stuff.
@Alaskanviking hehe I'm sorry, just trying to illuminate some options. Options = freedom, one with no options has no freedom. Don't remove options from your life on account of personal preference, quite often solutions arise in options unexplored. 👍