Is it time to Retire?

[SuperMex]

I am trying to get advice from others who have been in my position on when to punch out of work.

I retired from the Military at age 43 with 22 years of military service on 1 June 2015. I had a job already lined up and started the job while still on terminal leave.

My retirement from the military plus VA is $5300 a month.
I have two rentals that make about $500 a month pure profit, 10 acres of free and clear property in Florida, and several properties and rental homes in Mexico that are free and clear. (I don't count this income because I rent to Mexicans for almost nothing, they break even)
I have about $230,000 in cash and stock.
I am an only child and I stand to inherit roughly $1,000,000 of cash and property in the next 10 years.

I almost never spend more than $5000 a month.

My Current job pays $56,000 a year plus a stipend of up to $35,000 a year for housing, rent, electricity, water, garbage etc. (In actuality my total home expenses are around $24,000 a year that my job reimburses)

My son an only child is attending college he is a freshman I have allotted ($30,000 a year for this expense)

I have no other debt, I save around $30,000 a year.

I really like my job because I still get to help and mentor Soldiers everyday.

My question is not can I retire, I know I can. My question is given the three choices below which one makes the most sense and why.

1. Work until my son graduates college age 48. Total savings should be about $450,000 income of $7000 a month.

2. Work until age 56 this would allow me to collect an additional pension of around $1000 a month. Based on my current savings rate I should have about $1,000,000 in stock by then. This would push my income to $8500-$9000 a month. At SS age it would increase an additional $2000 a month.

3. Work until age 62 my additional pension would be $1600 a month. I should have about $1,500,000 and my income would be 12,500 a month.

Does the time out weigh the money?

[JLee]

Does the time out weigh the money?

Only you can answer that.

If I had $5k/mo in reliable passive income coming in I would retire today.

[makinbutter]

Does the time out weigh the money?

Only you can answer that.

If I had $5k/mo in reliable passive income coming in I would retire today.

Yep, cosign this.  If you enjoy work, why not see if you can mentor soldiers part-time?  Sounds like you get some personal fulfillment out of that.  But you have 5k in guaranteed income, cheap health insurance, AND you stand to inherit 1MM?

Sounds like quittin' time to me!

[Quidnon?]

I would chose #1, but I don't love my job, either.  See if you can stay on with a reduced workload and schedule, and spend more time enjoying your winnings.  You don't need to plan to die broke, but at the rate you are going, your kid is going to be the one with the early & long retirement.

[iluvzbeach]

Money doesn't seem to be an issue that would prevent you from retiring at any time. Unless you just feel better having more, work beyond today is not a necessity. That said, you clearly aren't working because you need the money. Only you can decide if you wish to continue working because of the satisfaction it brings and, perhaps, just a little bit of you feels like "he who dies with the most cash wins." Right now you're trading your free time for cash or the assurance of cash in the years ahead and that may be a perfectly fine exchange for you.

Personally, I'd be out right this moment and only "work" on my terms. Volunteering and very part-time, non-career work would be what I'd want. I'd spend the rest of my time on hobbies and travel.

[SwordGuy]

I would see if I could do the mentoring on a part-time basis if I really enjoyed it. 

(And thanks for doing that job and caring about it, by the way!)

Otherwise I would be out of there pronto.  You didn't clearly say how much you had in liquid assets.  Could you easily pay the college fees from those assets and still have enough to grow them up again?

[Simple1_2_3]

Congrats, you have excellent options and any  of these three sounds like a winner to me. Nope, I am still working - although the numbers say I probably can retire, but I am a little paranoid and I would like to think that is a good trait, maybe a prerequisite to achieve real FI. 

You obviously don't need to work  for money at this point of your life.  So the real question is what is your life's purpose now ?  Then, the so called "retirement date" should just fit in naturally.

 I prefer to error on the side of being cautious.  That's said, I will keep "working" until at least my son is on his own and won't need me for any emergency overage.  I personally, like to have a structured schedule and stay engaged with the rest of world is good for both my brain and my mental health.   I will  optimize my SS and pension earnings while I can;  the world is full of uncertainties and surprises.  Financial resource won't solve all my challenges down the road  but it sure will give me options and as I get older, I need all the options I can get.

Most of all, enjoy your "work".  You are making a difference for others and getting  paid for your time, efforts and skills.  What a blessing.  Don't forget to take care of your health,  None of the above means anything if you are not healthy.  Again, congrats, you have obtained the real "freedom"  as long as you are  spending your time that is meaningful to you - no matter what you do and when you actually "retire."