Looking to obtain more properties to own and manage while on retirement; a few years away.

I've previously made errors in investing and I do not want to repeat...so I'm hoping to get some input prior to going back in :-)  I have a fulltime job and a part time psychotherapy practice.My longer term goal is to make 5k per month for retirement.My medium term goal is to quit my job and do part time work. in order to to that, I have to pay back the $ I borrowed from by retirement fund or I have to pay major taxes.

I am interested to know how using a tax-deferred retirement account to purchase a rental would affect my ability to use depreciation.  

Answers will (and should) be different depending on what else you have going on in your life, your retirement goals, your real estate goals, etc.As far as cost saving measures, I am not really a flipper, so can't comment.  

One of my grandfathers retired at 37 and has lived on dividends from personal investments in stock and commissions from being a stock broker.

You've probably not had much exposure yet to retirement accounts and such, but they can be a huge source of funding for small businesses like real estate investors.

If I were already happy with my job I would hold the property in Hawaii until I retire.

If website prognosticators like me were always right we'd have sold in 2006, bought 3 years later, and be retired instead of writing here!

I have to take the time and effort to liquidate a deferred annuity (18,000) and empty a retirement account (5,000) and add it to ALL my savings in order to come up with 90,000, so I can offer 90,000.

I'm going to try "retirement" again when I hit $5000/month.