After its AOL division paid out an insane $850 million for social-networking site Bebo yesterday, one had to wonder if the true digital legacy of Time Warner (TWX) will be as the perpetual gravy train for legions of Web players.

It certainly seems that way, from the original AOL execs who “merged” their company with Time Warner in 2000 and cashed out at the peak right after the deal to the series of ad-networking start-up entrepreneurs who got acquired, took their payouts and skedaddled right on through to the two founders of Bebo–Michael and Xochi Birch–who didn’t even stay long enough for a latte after grabbing their chunk of the payday Time Warner was handing out in crisp bank notes for the social-networking site they founded.

And, more importantly, after one digital misstep after the next dating back to its Pathfinder days–which I have likened to watching someone fall down an endless staircase–one also has to wonder if Time Warner will ever see any of the upside of the Internet itself.

I remain dubious.

And after interviewing numerous sources close to the company yesterday after the Bebo deal was announced, I am even more certain of more trouble ahead.

Here’s why:

1. While I have always admired Bebo for its innovation and cool ideas about content (I love its “KateModern” online series, as you can see here), AOL essentially just forked over all that money for an audience of primarily teenagers in England, which is Bebo’s biggest market by far (but where Facebook has pulled to No. 1 in a year).

And while Bebo execs would argue with me about this, especially since international aspirations were touted by AOL yesterday, it has no more international traction than much more powerful leaders Facebook and MySpace. More significantly, its size in the important U.S. market, which is hoped will be helped by a marketing boost from AOL, is small and further traction remains questionable.

To be fair, AOL also touted the high engagement levels, which Bebo does have in terms of both minutes and page view per user.

2. Sources close to the company say AOL CEO Randy Falco and President Ron Grant–who are none-too-lovingly called Burns and Smithers at AOL–kept the deal a relative secret from most other execs, including those who might be majorly impacted.

It is not abnormal for acquisitions to be done in a tight group, but was apparently excessive in this case, and reminds one of the sneakiness of former Time Warner CEO Jerry Levin in the troubled AOL merger.

3. Sources said Falco had repeatedly told execs at AOL that he had to do a “big property” acquisition to move the needle, which has not been exactly moving at the unit of late, in order to show Wall Street that AOL had a social-networking strategy. “It’s like constantly scrambling eggs, by doing big new moves, you can hide the problems,” said one exec.

4. The turmoil in its online advertising unit, dubbed Platform A back in the fall, is real and profound and extraordinarily troublesome, given that it is supposed to be the engine to make the Bebo financial projections work at AOL. As I wrote earlier, Bebo needs that jump-start given its small revenues and profits.

The recent departure of three of the key executives who were supposed to be part of Platform A’s success–VP of Marketing Solutions Kathy Kayse and EVP for Global Advertising Strategy Dave Morgan in February, as well as Platform A President Curt Viebranz last week–is worrisome, even though it has been floated by AOL as a housecleaning.

But, curiously, all get good marks for competence from many and had, in fact, been recently touted as saviors by AOL. They do share one thing in common, said several sources: Run-ins with Grant, over cuts in spending and disagreement over aggressive sales projections in a recessionary economy.

In addition, all the key execs from its Tacoda acquisition are gone, along with those from its Quigo buy.

And, while its Advertising.com top exec Lynda Clarizio has taken over Platform A and is considered a strong exec and a “go-getter,” many sources told me she also reportedly had similar testy run-ins with Grant, before he recently was quoted on her promotion: “There is no one better qualified to do this than Lynda, whose track record at Advertising.com has been nothing short of stellar.”

While corporate departures and infighting are also common at many companies, especially over budgets and performance expectations, the level of rancor at AOL has been high.

5. Perhaps most importantly, it remains a mystery to me and many others I talked to yesterday that AOL has not truly attempted to take its very powerful properties like AIM and ICQ and make them more social, building applications on top of already robust ones and partnering around the Web.

“Didn’t AOL invent the social graph with Buddy Lists?” said one perplexed Silicon Valley luminary to me. Yes, indeedy, it did.

Thus, I am still trying to figure out why AOL–which was built on the pillars of community, communications and connectivity–has consistently not been able to leverage its still-valuable assets.

I suppose it is sexier to do a big, splashy deal, of course, which takes focus away–for a while at least–of the essential need to take hits, while doing the slow block-and-tackle work it will require to really build a strong ad and social network.

Buying Bebo, the third-ranked social network, for so much and trying to turbocharge it is a very lofty goal, of course, but the real problem with the acquisition is that it feels like an answer in search of a question.

While Bebo President Joanna Shields–who will enter the AOL exec team as part of the deal–and the Birches have clearly built a very interesting property, the weight of Falco’s calling it a “game-changer” on which AOL’s future rides could turn out to be much too much for Bebo to carry.

That is, especially with that heavy bag of Time Warner cash it is also shouldering.

What’s AOL getting for its $850 million in cash to purchase social-networking site, Bebo?

A very attractive social-networking service and a very experienced exec who has been running it.

But, perhaps more importantly for those who focus on pesky numbers, not a whole lot of revenue and negligible profits, judging financial information I got a gander at, courtesy of sources at several companies that looked at funding or buying Bebo.

And the rest of the overall outlook for Bebo? A small but growing business, with nice user engagement with strong page views and minutes spent per session, but little traction beyond Britain and Ireland, and too small a presence in the critical U.S. market.

(Bebo is also strong in New Zealand, but BoomTown does not have to point out that that country is not exactly the kind of game-changer that AOL CEO Randy Falco mentioned in his email to the troops about the purchase.)

According to the several sources who were privy to Bebo’s financials, for example, Bebo’s revenues for 2006 were only $7 million with $3 million in EBITDA (earnings before interest, taxes, depreciation and amortization). In 2007, the results are still small, with $20 million in revenues and $5 million in EBITDA.

Using 2007 results, that means Time Warner’s (TWZ) AOL paid a handsome 42.5 times revenues and an incredible 160 times EBITDA.

AOL might assert that it makes Bebo a bargain, given that Facebook got valued at 50 times revenue when it got that $15 billion valuation from the $240 million investment from Microsoft (MSFT) last year. Still, Facebook has a huge presence in the U.S. and is growing strongly in Europe, including being just ahead in Bebo’s strongest territory in the U.K.

Projecting outward, the company estimated–remember, these are not actual numbers, but a best guess by Bebo execs–it would have $50 million in revenue and $10 million in EBITDA in 2008; $117 million in revenue and $48 million in revenue in 2009 and $193 million in revenue and $92 million in EBITDA in 2010.

While potential is important, the high price (which was still lower than the $1 billion and above that Bebo might have fetched even six months ago) and its small presence in the U.S. were the reasons several companies passed on acquiring Bebo–including News Corp. (NWS), Google (GOOG), Yahoo (YHOO) and CBS (CBS), said sources close to each of these companies.

On the plus side, users do spend a lot of time on Bebo, engaged by its more robust content offerings, such as its “KateModern” series (which I wrote about here), and its elegant and content-rich offering, which has some of the cleanness of a Facebook and some of the flash of MySpace.

In addition, in Bebo’s president Joanna Shields (pictured here somewhat awkwardly shaking AOL CEO Falco’s hand and with AOL President and COO Ron Grant), AOL gets an experienced and savvy Web exec, which it desperately needs these days, given the flux there.

Shields has worked at RealNetworks and Google and she will continue to run Bebo and report to Grant. In fact, Shields has effectively been running Bebo for a while now, and its founders Michael Birch and Xochi Birch will be leaving the company.

You can see Shields in action in this video, which I did while visiting London last summer: