Banks definitely lend easier with a stable W-2 income, so I plan on keeping my job as long as possible to get my boat closer to the dock before I jump ship.

Whether your are a flipper or a BRRRR investor higher interest rates will in a stable market (not including places like Seattle and Denver in this conversation) lead to declining sale/appraisal prices and allow you to cash out at a lower % to ARV in order to meet your cashflow needs. 

If you can prove stable and predictable income then you should be good.

Look for a middle aged family person who is a real estate sales person, preferably a retired contractor or  with a spouse who is one.

You could have the owner hold a purchase money mortgage, you could partner with someone who has cash, buy an home with a retirement account, ect.

I'm trying to say that I'm financially  stable and saving at least $500 every month but still don't have a lot saved.

I don't want to work for someone else until I'm 65 and end up like my dad who is 63 and hoping the stock market will not mess up his retirement. 

It all depends on how much income you're making now, how much you intend to be making in retirement and how you can best use your current resources, and what your plans for the future are.  

@Drew Markert: ~10 years from now, I hope to of transitioned to a full "hold" position and be able to retire a little early, or at the very least, afford my vacation/future retirement home with the profits/income, if things go well.  

Long term goals are to produce more income for when i retire and to eventually be able to quit my job and focus full time on investing.