Boeing's Lucky Number: 7? 8? 7?

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"The woods are lovely, dark, and deep,
But I have promises to keep,
And miles to go before I sleep,
And miles to go before I sleep."

I realize it's a little late for entry in the Fool's Poetry Month competition, but Robert Frost's poem seems especially apropos today in relation to Boeing's (NYSE: BA) big announcement. On Thursday, the aerospace giant ignored my advice (and not for the first time), boldly going where it's so often gone before ... namely, out on a limb.

How far out?
About a year. Reading from the press release: "the first flight of the 787 Dreamliner is expected by the end of 2009 and first delivery is expected to occur in the fourth quarter of 2010." Within three years after start-up, Boeing expects to be building the things at the rate of 10 per month.

I suppose if you're a Boeing customer, that's good news. All Nippon Airways should begin seeing the first units of its 50-plane order arriving on the tarmac in a little over a year (albeit two years overdue). Meanwhile, suppliers like Honeywell (NYSE: HON), United Tech (NYSE: UTX), and Spirit AeroSystems (NYSE: SPR) now know that it will be 2013 before they can really ramp up their 787 fulfillment operations and generate revenues as Boeing cranks the planes out.

It's going to be a long wait, but here in investor-land, nobody's interested in waiting. To the contrary, they've been chomping at the bit for good news, and bid up Boeing shares 8% in anticipation that "the worst is over."

Not so fast
Pity Boeing doesn't feel the same. In conjunction with its new timeline, Boeing released a damage assessment on the delays already incurred. Specifically, multiple tweaks and revamps required to work out the kinks on the first three 787 models have rendered them essentially unsaleable. Boeing is therefore reclassifying each plane as an exercise in "research and development" -- rather than as "inventory" eventually to be sold. The long and short of this is that Boeing's taking a $2.21-per-share pre-tax charge to earnings this quarter -- turning an expected profit into an almost certain loss.

As bulls grow horns, analysts bare claws
Investors may be shrugging off the earnings warning as "just numbers," but companies who make it their business to worry about numbers aren't nearly as sanguine. In the wake of Boeing's announcement -- at the same time as investors were buying Boeing hand over fist -- two credit raters chimed in on downbeat notes.

Standard and Poor's expressed skepticism that all is now well with Boeing. While S&P had already factored a 2010 delivery date into its credit ratings, the credit rater points out that delays that have already happened can still hurt Boeing.

Specifically, S&P fears that even if Boeing keeps its latest promise, we could see further cancellations and deferrals of not just 787 orders, but also other models such as the 737. Current customers like Delta (NYSE: DAL), Continental (NYSE: CAL), or AMR (NYSE: AMR) could follow the route Qantas recently took -- canceling some orders and deferring others as they discover that planes they absolutely had to have two years ago, no longer seem essential in an era of declining air traffic and cash flows stretched to breaking. The longer Boeing waits to begin executing its side of the sales contract, the more chance customers will rethink their commitments to their side.

Miles to go
Next door at Fitch, the concern is more immediate. Fitch points out that Boeing has "doubled" its debt load over the past six months. This puts the aerospace giant in a parlous state, as it begins to spend on the parts it will need to begin building 787s. Fitch warns that we could see Boeing's capital needs burning cash all the way from now through the end of 2010. Boeing's got many "miles to go" before investors can sleep soundly again.

And then there's the unspoken disaster scenario: What if Boeing, debt-laden and burning cash, fails to meet its latest deadline -- postponing positive free cash flow even longer? No ... that's a fate too dire to think about.

Foolish takeaway
Six times Boeing has set a date for delivery of its ill-fated 787 Dreamliner. Six times, it's failed to deliver. For all our sakes, let's hope the seventh time's the charm.

Robert Frost never said that "it's always darkest before the dawn," but it well could be. Is now the time to take a gamble and buy Boeing? On Fool.com, we report, but at Motley Fool CAPS you decide. Click on over and tell us what you think.