If you had no U.S. income in 2009 and had no residence here then it does not seem as if you were required to file. If you are worried about a naturalization application down the road I think you will be able to adequately explain the situation.
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Since your priority date is well before the cutoff date listed in the Visa Bulletin as of October you can file his I-485 at any time. Be advised that these dates are different depending upon which country you come from but at this time there do seem to be visas available for your preference category with your priority date. You can check this at the Visa Bulletin website at the Department of State.
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You can only petition for the maid as an employer and would then have to satisfy certain Department of Labor regulations. She cannot come in on a visitor visa. This is quite complicated and I would advise that you speak with an experienced immigration attorney in order to evaluate options for resolving this matter.
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There is no way to say what will happen in your fiance's situation or even the possibilities without more facts about your particular situation. In general Immigration Judges have a lot of discretion when it comes to what sound like aggravated felonies, even when carried out by y.o.'s. In any case you will need the assistance of an immigration attorney. I am located in Manhattan and if you would like to discuss your case, please feel free to call or email.
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If you are here and you get married here you can file here, however, you won't be to go back to Canada to live. You need to reside together and prove that your marriage is not fraudulent and it will take time to process your application. You can apply for an Advanced Parole travel document while your petition is pending but that would be for short term travel.
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It's actually more important that your future wife is up to date on her taxes and that you have sufficient income to meet the public charge requirements. It won't make any difference when you get married in this situation and you are always able to make arrangements to pay your taxes on an installment basis.
A citizen can petition for their spouse to obtain a conditional Legal Permanent Residence (Green Card). 2 years later, you would apply for a 10 year green card, and after 3 years you can apply for citizenship. Depending on your particular circumstances you may be able to adjust your status without leaving the country but you should speak with an experienced immigration attorney who can evaluate the details of your case.
Usually, someone on an F-1 can move to an H-1 if their employer fulfills the Department of Labor/Immigration requirements. Since there are nursing shortages everywhere this seems likely, that being said each case is different based on the background of the individual.
I would just like to re-emphasize that if your husband does not have an I-94, proof of entry and inspection at the U.S. border, he will not be allowed to adjust status, regardless of how legitimate your marriage is. As suggested above, you should consult with an experienced immigration attorney to sort this out before you file.
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You must provide all current and truthful information. The criminal/court records will be matched to his fingerprints in any case.
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