@Jake MiresYou want to see if you are eligible to claim real estate professional status or if your total income is below $100,000 which will allow the $25,000 passive real estate losses to go through.The thing that sucks about Business income / Independent contractor income is that the income is subject to federal taxes, State taxes and self-employment taxes.You may also want to consider a retirement account(SEP IRA).Best of luck.

Is there anyone who has tried using their ROTH IRA to invest outside of the country?

This will help reduce your taxable earned income, but there are legal methods to use IRA money to invest in RE. 

The repayment terms for a 401k participant loan are equal monthly/quarterly payments of principal and interest (typically prime plus 1%) over a 5 year term (longer if used to acquire your principal residence).Please note that if you take a full $50,000 and then pay back the loan, you can't take another $50,000 until 12 months after the first loan was fully paid back.Per the loan offset rules that went into effect with the 2018 Tax and Job Act: if you leave your job and the loan is current at the time you leave your job but then the loan goes into default because you left your job, you will have until your tax return deadline (including any timely filed extension) to make the loan current by depositing the outstanding balance into an IRA (and thereby avoid the taxes and penalties that would otherwise apply). 

I am looking to convert my captive IRA (i.e., only allows me to invest in stock/bonds) to a self-directed IRA, so I can use those funds to purchase properties.

It starts with a self-directed IRA held by a custodian, but the IRA simply makes one investment into a specially designed LLC entity.

(Ask me sometime why I think 401(k)s and IRAs are a horrible idea because they lock up capital people could be using usefully.....well, actually, don't. :)  )It does seem like it may be a valuable tool as I move into buying apartment complexes and commercial buildings in the next couple of years.

Many members are experts in their respective fields related to real estate investing, whether that is real estate brokerage, wholesaling, flipping, buy and hold, lending, self-directed IRA and Solo 401k investing, or tax and legal guidance.There are some pretty cool discounts on various products and services offered as Perks to BP members that you might want to check out: https://www.biggerpockets.com/perks/proIf you haven’t checked it out already, the Bigger Pockets blog features links to their awesome podcast and many great articles: https://www.biggerpockets.com/renewsblog/The site has quite a few tools that can be helpful for new members.

Hello, I have a questions about self directed IRA.

If I had to hold 1 year of 401K/IRA investments to make it happen would it be worth it?