What made you interested in investing in this type of deal?

@Michael Doughty I think @Julio Gonzalez has made some solid points here.

What made you interested in investing in this type of deal?

I personally don't like 401K's as you are likely paying for 'management fees' within managed funds and likely some admin costs for holding assets inside a 401k.I think you made the good choice moving it over to an IRA.With that said, I will be biased as I don't like retirement accounts / equities and I think I can perform better with real estate than the stock market.If you can get into a good real estate investment that makes 5% more than you would in equities / retirement account, it may make sense.I think the issue you have is that you don't have experience in real estate at the moment, so you are unsure of what your return would be.

In order to account for the cost/risk of your rental payment, I would measure it based on ($ cash flow)/($ rent).

I know that I’ve left a lot of money on the table as I could have rented my house out long ago and made  quite a bit of money.

I've made a living out of trading before.

Since I’ve made that parallel I’m trying to find ways to not kill the “honeymoon period” but also set myself to survive and begin learning the skills I need to evaluate deals while I save up cash.here are my main concerns:1.

The appreciation and principle pay down is where all your wealth will be made. 

Keep your finances in order.