Ok, so I did not take the time to read through every reply, so excuse me if something like this has been brought up already.
My take, although a bit more reserved than it may read, start anytime you feel you are up for a very heavy challenge. The economy of course is very real, but we are in an industry that is comprised of wants & needs from clients. Currently the "wants" are tapering because of the economy, but there are still the needs.
Rule 1, keep your overhead as low as you POSSIBLY can! Used equipment, no fancy new trucks etc., bare bones minimum to get the work done safely. No client of mine has ever known that my chipper was a 1984 with 10million hours on it, they just plain don't know the difference. They just saw how great the trees looked and how clean the yard was.
Rule 2, use a small marketing dollar wisely. The best marketing dollar you can possibly spend is on fuel. (see rule 3 for details)
Rule 3, don't sit back in your home office (no fancy shop) with your size 10's kicked up on the desk waiting for that next lead to come in. Get out there and find the work (this is where fuel as marketing comes in) Pound doors!!
There is so much work out there that NEEDS to be done. And a ton of that work needs to be done no matter what the economy says. Commercial properties & condo's, apartments etc. Sure, you are going to have to come in extremely low in your bids to get them, but it's income & getting your name out there.
Pound the hell out of doors, work your butt off for minimum pay, make those contacts! Those contacts will not forget who you are if you do honest work at good rates, and when the economy starts to make a curve for the better, you will be seeing so much refferal business you'll get dizzy. Meanwhile the guys who were not willing to work really hard for shorter $$ will be out of business, and you could be a front runner in your market so when the people start spending again, you'll get the lions share!
I know of 3 companies that have folded in my local market in the past 2 months. I sold $34K in the past 6 days, $8K came from our local yellow pages.
Of course this theory only works with honesty & integrity.
If you look back to the great depression, think of where the wealth was built back up from. Sure, some old money, but for the most part it was built back up with a ton of hard work & ingenuity.
You can do it man.
My disclaimer: I did not share this viewpoint to offend anybody or to spark debate, its just how I feel.