@James Maness, If the properties held in your IRA produce enough income for you to live on - you could access your retirement funds prior to normal retirement age without penalties.

As a newbie  investor (at the ripe young age of 61), I'm formalizing my goals at 1,3,5 and 10 year increments - so your post title hooked me!

The properties are on Cleveland's west side in Ohio City South of Lorain and in Eco Village South of Gordon Sq. so they are definitely older in age.  

It's amazing that you are looking to get into investing at such a young age.

The chance that you risk it all, lose, and have to start over at whatever age you are in life? 

In age where single people making decent incomes get KILLED in taxes while trying to make a life for yourself.

The age of that house may make a difference. 

I get paid very well for my age in a corporate job I don't like and hustle my *** off doing REI on the side to build up my business (so believe me, I feel you).

Where I am currently - So currently I'm 29 years of age married 3 kids.

We'll cut to the chase, here's our dirt.The Facts: Ages 51/44, Married, w/10 yr. old childOne steady income 45KOne low income & fluctuating (self employed only 2 years but growing slowly)Living/ renting in NJ (Very expensive market, 2 family units sell over 500K)Fair amount of debt 37K (Car loan, 2 CC, Medical bills)Just getting by each monthCombined 401K's =  150KMy 401 (100K) can be transferred with no penalty to a self directed IRA (I had opened up last year in hopes of using some cash to invest in RE) We are determined to get into REI however we're probably going to need some creative ways to do it with our current situation.