I'm marrying a talented and down to earth woman later this year, but our assets are wildly different. I've been (unwittingly) practicing the principles of Mustachianism since I was in college (now 31), graduated with no debt and have since amassed about $330k in taxable accounts and 100k in retirement accounts. Net worth: 430k. In retrospect, I made a ton of mistakes and if I had done everything right I could be financially independent today.
My soon to be lovely wife, however, has a $270k student debt at roughly 8% all federal, but she qualifies for income based repayment (IBR). She has one more year of residency, and by the time she is finished with her residency she will have completed 4 or the 10 years necessary at a nonprofit for loan forgiveness. She will be able to reasonably make about $170k/year when she graduates. She has not yet fully embraced Mustachianism, so our expenses are a little higher than they would otherwise be, but she loves her job (for now). Our expenses are relatively high at about 55k per year including loan repayment and payments on a 120k mortgage. We own both used cars. I would drop down to one car, but my hobby (playing music in bars late at night for tiny amounts of money) isn't compatible with her occasional long hours.
My personal job satisfaction has dropped substantially in the past couple of years for a couple of reasons, and I'm considering taking a big pay cut (from 70-80k or so) and doing freelance work (unknown $$, $40-100k depending on how hard I network and work?), however if we file taxes jointly, any income I make will increase the expense we have for paying back her student debt. We technically do not have to pay it off entirely, and the maximum payment we have to make is the payment to pay the loan off in 10 years. When she takes an attending physician's salary, we will probably be paying the maximum payment, but since she has already done 4 years of nonprofit service, the loan will vanish with 4 years remaining to pay. To make things even more complicated, i'm in a "Community Property" state, and if we file separately 50% of her income is counted as mine and 50% of mine is counted as hers. I feel like I'm going to end up having to pay a tax professional to be able to handle this.
My question is: where to go from here?
1. Plan to pay off the 270k loan through IBR filing jointly (seems like a bad idea, skims 15% off my personal income and dividend/interest income)
2. Pay off the 270k loan through IBR filing separately which seems like it will be a tax preparation nightmare
3. Pay off the 270k loan as fast as we can, this would deplete my 'stache and make the prenup agreement much more complicated since I would effectively convert part of my 'stache into marital property.
4. Pay off the 270k loan as fast as our incomes and savings will allow, trying to finish and pay the extra before the 7 years are up at which point it would vanish
After we're married we also have to figure out where to put any new investments: new home mortgage in a new city, joint investment accounts, etc. The loan repayment situation makes holding joint assets complicated for filing until we exceed the 10 year repayment maximum loan payment on the IBR with our combined salaries and investment income.