Advice On How To Proceed With My Weird Life?

[Fiddler]

What I'm about to tell you is the unvarnished truth in a nutshell. I don't have any living family or close friends to confide in, so I'm going to ask you truckers for advice.
I'm 56 years old. I spent most of my adult life as a nightclub musician. It was fun until M.A.D.D. and karoake came along. Now it's over.
In the Spring of 2005 I attended Sage Truck Driving School. All of my classmates were trying to start over in new careers, like me. After I graduated, I tried to work for a flatbed company. The tarping got me. I kept having fainting spells in the 100+ heat while trying to tarp loads and was fired after only six weeks. I could never work in the sun, and knew it, but ignored this fact in my enthusiasm to be a flatbedder.
Then I came back to Florida and got a job driving a dump truck. This was much more to my liking. About a year into it, a bolt from the blue struck.
The last of my living relatives died and left a small fortune. I wasn't in anybody's will, being the black sheep, but, seeing how I was the last surviving blood, I inherited the whole kit and kaboodle in probate.
So now I'm living in a paid-off house on a river out in the country. I inherited an almost-new car. My poor sister only got to put 604 miles on it before she died. There's $108,000 in the bank account. I don't have any family, children, debts, or much in the way of monthly bills. A monthly telephone bill and power bill. And a yearly IP service provider bill ($7.95 a month for Toast.net) That's it. The main thorn in my side is the property tax! :x
Anyway, while it would seem I'm "sitting pretty", I do realize I have something I need to deal with. My dump truck driving job went bye-bye a year ago because of the local construction crash. Nobody is hiring anymore.
While I'm far from desperate, I do realize I've got to get moving again. I don't have enough money to retire completely. Besides, I really would like to be trucking again. I've got a squeaky-clean Class A CDL, but I'll be trying to make a brand-new start at the age of 56 with very little over the road experience. And it's been almost three years since I was in school. Would anyone even hire me?
While I'm sure I've got enough money to pay cash for a good used tractor, should I? I've read on this forum that a brand-new owner/operator with very little experience stands very little chance of getting loads and insurance.
What would you do if your were in my place? Should I forget about trucking altogether?
Any and all advice will be read with great interest. Thanks.

[Roadhog]

I would continue to seek a local driving job, even if it is part-time. Your main concern is covering your expenses and not whittle away your savings, and keep a health insurance policy. Once you get past the economic crunch, better jobs like dump trucking will open up again.

Don't get involved in buying your own truck and working under someones authority. You lack the experience, and it is tough right now even for those who already have a network.

You only need to keep busy for 10 more years, and you can apply for full retirement, and sign up with Medicare. Stick away as much money as you can and add to your savings, and start an IRA. You have a substantial savings, and should see 5-7% increase regularly in interest. Your property tax will be offset on your tax return. The property value will increase steadily as well, and if worse comes to worse in your retirement age years, you can do a reverse mortgage.,..after all, you can't take it with you.

Keep yourself active and happy, and see a Doctor at least twice a year for blood work and routine physicals. Take up golf, and buy some nice sunglasses and go to a beach where there are hundreds of girls in bikinis. You will feel younger, and you will think like a 20 year old.
Stay out of jail... don't get married... get a pet... take a nice travel vacation once a year to satisfy your need to go down the road.

And, hire a Brazilian 24 year old live-in housekeeper, if you really need some drama in your life. 8)

[Fiddler]

Hey roadhog, thanks for the quick response! I think you're right in saying I'd get in over my head if I bought my own rig.
By the way, I quit going to the beach and girlwatching years ago because all those hideous tattoos and piercings make me depressed. Such vandalism of perfect young white skin!

[ICS]

Everything that was said in these posts are great advice... well excluding the part about the tattoos. :P