Ok, I have been kicking this around for about 2 months now.
I sold my business back in August and would like to get into trucking. I'm 52 and in very good health. I have a few questions.
1. Am I crazy to even consider this at my age?
2. What's the best way to become licensed? Tech school, sign on with a company sponsored school or is there a way to get the CDL on my own?
3. If I can get it on my own, how hard will it be to get a job?

Thanks in advance for all your advice.

This depends on you personally. If you have the desire to drive a truck then no you aren't crazy. Driving requires a lot of long hours and many sacrifices but if it's something that you enjoy then it is worth it and no you aren't crazy.
Best way to become licensed. Well that also depends. Personally I don't believe that anyone should pay to get their CDL. There are entirely too many companies who are willing to pay for it. The only downside though is you have to give them xxx amount of time. CRST, I believe is the shortest with 8 months, but that would be team driving (something I wouldn't recommend unless you have someone you already know and can co-drive with) but the average is 12 to 18 months with some companies as much as 2 years.
Snap your fingers and you'll have job offers. If you have a fairly decent driving record and a CDL then truckload companies will hire like mad. The driving industry has such a high turn over rate that companies simply can't afford to discriminate against drivers based on where they obtained their CDL. However if you do get one through a company it may be a bit easier as you will know that you definitely have a job once you complete your training. Look around and do your homework. Check out the companies. Not all companies are for everyone. Driving can be a rewarding career but it's not for everyone. Make sure you look below before you jump and good luck to you. Hope this helps you on your search for answers.
Cheers

Your age should not be a factor. If you are willing to listen, learn, and travel while earning money then your in the right place!

Going thru an accredited truck driving school should be your first priority. Wether you get training through your local job service with a grant, pay the money out of your pocket for schooling, or sign on with a large carrier that will foot the bill for your training, will not really matter in the long run. The key is to get the training and get in the saddle asap.
In the event you choose to pay for the schooling yourself figure on tuition costs of 2500 to 7500 for a course that may be as short as a couple of weeks to a course that may be several months.
This amount of money is an "investment" in your future and should be viewed as such. You will make 35 to 40 grand in your first year of trucking so the sooner you get started the more you will make. Do not forget that trucking also offers great benefits such as Medical, dental, vision, disability, 401k, vacation, etc.

Age is really not a factor, I started at 64, check the school before attending, most are CDL Mills, a lot of standing waiting for an Instructor. No matter what, if you do this, pick a Company that you will stick with for a minimum of 6 months to 1 year, then you have an open door for any Company, do your home work,,,,,, Good Luck

Thanks to all for the good advice. and Happy New Year!!!!!