Originally posted by autoxer
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I don't have a crystal ball, but I do believe that interest rates will rise in the future. This shouldn't change your comfort level with different investment classes and it won't preclude the ability find good real estate investments. The interest rate on the loan is just one of many costs associated with a rental property, so I wouldn't single that out as a reason to move into a different asset class. If interest rates do rise a couple points, you aren't all of a sudden going to be comfortable with stock markets, you might just look for different things in a real estate investment.
To be upfront, I am more comfortable investing in stock markets and don't have much interest in real estate. I don't necessarily think that investing in real estate is bad, just not something that I'm comfortable with.

I don't view my 401k money as being stuck, just set aside for the future. If I was faced with the option of taking a 401k loan, then the no brainer solution for me would be to wait and save up more. I just started saving up for a down payment on my next house and although I could liquidate my brokerage account and make the move right now, I would rather leave that money invested and save more from my cash flow until I have enough money in my savings account to put 20% down on my next house.
We were not going to buy the house soon, but I decided to bite the bullet in 2013. We were paying high rent (almost 2K a month for a 2 bedroom apartment), and I was timing the market. I probably should have bought an year earlier (not possible since I was totally cash strapped), and buying in 2013 was not a bad choice in the hindsight. In the DC metro area, prices have continued to rise steadily since then.
Another reason to buy in 2013 was that 2014 was our true deadline. My daughter was going to start her kindergarten that year. I didn't want to wait until 2014 and put ourselves under pressure.
Most importantly though, we really liked the house we saw. It did have a few issues but overall, we have been very happy here and it turned out to be the right call as far as the house itself goes.
I like my new car, even though I know it wasn't a wise financial decision. If you can reduce future depreciation and/or get something more fuel efficient and be happy with the decision then consider selling them, otherwise just pay them off and keep driving them.
You don't necessarily have to eliminate all debts before taking on another mortgage, if you are comfortable with the cash flow, but it would certainly give you more flexibility. Freeing up cash flow allows you to plan more for the future, instead of paying for past decisions. Just keep in mind that using debt strategically to leverage appreciating assets is good and depreciating assets are bad, whether they are financed or not.
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