Trying to decide if I can FIRE now (any advice will be greatly appreciated)

[retiringearly]

Hi - hoping for some input/advice.  I am trying to decide if I can retire right now.

Specifics:
49 years old, never married, no kids.
Own my condo with no mortgage (value approx. $200K)
Have 4 single family homes as rental properties (combined mortgages approximately $240K, total value of the 4 approximately $340K).

Investments outside of real estate:
$457K outside of retirement accounts
$367K in traditional IRA
$129K in inherited IRA
$286K in Roth IRA

I can definitely live on $50K per year which is approx. 4% of my investments outside of real estate

I am nervous about getting to age 59.5 on my investments outside of the traditional and Roth IRA's.  I can draw on the inherited IRA with no penalty (just pay income tax), I do not believe I can draw on the Roth IRA because it was a conversion that I did, I never actually contributed to it due to income restrictions.  The amount in the Roth started as a traditional IRA that I converted and paid the tax on about 7 years ago.

I have a ton of fears about this.  I am miserable in my job and have been for a long time.

Any insight/advice would be greatly appreciated.

Thanks

[catccc]

What kind of income do you get from your investment properties?  What would your healthcare expenses look like in retirement?

Regarding getting to 59.5... have you considered Roth Pipeline or SEPP (rule 72t) as drawdown methods?

[retiringearly]

Thanks for the input so far, I really do appreciate it.

I am including health insurance and related expense in the $50K per year.  It looks like a bronze or silver plan will cost me approximately $6k per year, I added in an additional $1K for out of pocket expenses.  I am healthy, non-smoker, weight is proportional to my height, etc.

I am definitely in an expensive area.  My property taxes are about $3,400 per year, and my HOA are about the same.  Moving to a county/town with lower taxes would definitely help.

The rental properties are about a break even in terms of cash flow while I have mortgages on them. 

[Bicycle_B]

Write your resignation letter and turn it in.

Based on what you wrote, just selling the existing non-retirement investments over a 10 year period would cover your cash flow needs until 59.5, even if a below-average investment environment produced zero returns on the portfolio for a decade.  You will find yourself using more efficient techniques than that (another poster already mentioned the Roth ladder), but the point is that the cash flow problem is solvable in numerous ways and you have lots of wiggle room.

[boarder42]

you're done congrats. 

[catccc]

I think you are in good shape.  Enjoy!

[retiringearly]

Thanks for the replies.  Especially the comment about retiring to a lower cost area.  I looked into homes in the town that I got my graduate degree in.  I am stunned at how much less taxes are.  And I love that town.

This was very encouraging!

Thanks!