But I have one major obstacle which prevents me from starting my real-estate adventure.

Do you prefer to buy detached homes or homes that are in the middle of the row of houses?

Colonial,  car detached garage, large back yard. 

So that 1k/mo actually was enough to cover all my expenses, and I had enough cash on hand to pay off all my (non-mortgage) debt.Of course, I wasn't getting ready to quit investing, so instead I used part of that cash to acquire a triplex in Muncie, Indiana, which adds another $800/month to my cashflow.Additionally, I rented my recording studio (built into a detached garage behind my primary residence) to another engineer/producer here in Nashville.

A potential big disadvantage is the age of the HVAC (1993) and Water Heater (1996) and the garage (detached) will need a roof before too long (within 3 years) Inside isn't bad, could use some paint and few other improvements.

My obstacle was getting contractor to bid on these types of jobs because they scope of work/estimate has to have the labor and material separate and itemized, which, contractor are not accustomed too. 

If so ,what were some of the obstacles you've had to encounter ? 

Imagine 3 newbies partnering on a detached triplex with each unit having its own yard. 

I don't know if I am seeing all the obstacles and traps I need to be wary of.  

Given your husbands background in construction, I would personally consider looking into a small multifamily (2-3 units) detached or semi-detached property in the city, that needs some work.