Once I get to a point that it is making enough per month that I feel comfortable taking money out of the business that would be when I get to the point that it is worth have a specialist assist me in all deductions, credits, and future items that will help me to transfer from a W2 to working for myself fully.

The lessons you learned the hard way in 2008 will be invaluable now, and it’s great that you’re aiming to stay small-scale and within your comfort zone of Sacramento, which gives you an advantage of knowledge in that market.Given your experience, I'd say start by focusing on three key areas to build confidence and minimize risks:Budget Control: Over-renovating was one of the big mistakes you mentioned.

Vestin Mortgage was the poster child for this.

I think real estate investors in the game just become confident as to handle new challenges and they call that being experienced - Just like parenting: you think you are experienced with changing diapers, but the child is growing-kindergaten-grade one-baseball/soccer- soon teenage and the jazz goes on - grandparent

I went from barely breaking even to walking away with a very comfortable profit.This experience taught me two critical lessons:Never give up when the situation looks bleak.

Just make sure you guys are comfortable with the area before pulling the trigger.

It is a matter of getting out of your comfort zone a little bit but not so much that you will burn out or lose sleep.

Provided I can establish a solid investment plan tailored to their financial needs/comforts such as debt ratios and income, they would be more than happy to offer me some financial control.Additionally, If I wanted to, for the sake of building my own personal wealth, I admittedly have the luxury of taking a loan from my parents.

Jaron Walling said something that caught my attention, "search for and buy a bad roof, leverage it during the negotiation"....especially of the property has been sitting on the market longer than normal for the current market, a "bad roof" might be a gift from the real estate genie.My point is this: get good at estimating and fixing a bad roof (or any particular problem found with most houses that sit on the market longer) and you'll get comfortable buying/fixing properties that scare off other buyers. 

Society and demographics favor smaller units since marriage and child bearing are being delayed.