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Besides the multiple practical problems with this approach (including the fact that the woman has to agree to accept the Mitzvos or you have to sell away her within a year, at which point, why won't she just convert?), the Rambam writes (Hilchos Havadim 3:6[4]): אין עבד עברי מותר בשפחה כנענית, עד שתהיה לו אישה ישראלית ובנים, אבל אם אין לו אישה ובנים, אין ...


Let's tweak the question a bit. Suppose a non-Jewish woman wants to convert, and meanwhile there is a Jewish mamzer who would like to get married. Can she do a quasi-conversion such that theoretically her status would be "Canaanite maidservant", at which point she'd be allowed to marry the mamzer? Rabbi Aaron Soloveichik insisted vociferously that the US ...


You could not circumvent the obligation, as an Eved Ivri remains obligated in positive time-bound commandments. (An Eved Kena'ani is not, but to make your plan work you'd have to first become a Kena'ani.)


Someone can be made Eved to pay back for something when he has no money, not necessarily bought with money.


Part of Ramban's comment on Breishit 32:21 offers some insight to this. He says that when Ya'akov sent messengers with a huge gift for Esav, the verse explains part of Ya'akovs thinking where he uses the term "kaparah" - a bit of an unusual term, here. Ramba"n explains that he sent servants before him and gave "kofer nafsho" (loose translation - redemption ...

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