Lehman Brothers (NYSE: LEH) just can't catch a break.

News of an impending buyout is usually some of the best news investors can hear. Share prices typically rise in anticipation of an offer coming in at a premium, and can sometimes soar even higher if investors think a bidding war will ensue.

But as we've learned in recent months, when it comes to gossip, Lehman seems to always find itself on the rotten end of the rumor mill.

Shares tanked around 11% Monday on rumors that British bank Barclays (NYSE: BCS) would make an offer for the troubled investment bank at a price below what it was trading for, although the target price isn't known.

Rumors and gossip aside, some critical questions have to be addressed before Lehman could be picked up at these battered prices. Here're just a few.

Shareholders are already fuming
When JPMorgan Chase (NYSE: JPM) made a last-ditch offer to pick up Bear Stearns in March, the initial $2-per-share offer was quickly scoffed at, to the extent that JPMorgan had to quintuple the offer soon after.

With Lehman shareholders already a bit peeved by short-seller attacks and a constant barrage of rumors about its ability to survive, it's unlikely they'll accept an offer that comes in at astonishingly low levels.  

What would happen to financial markets?
By many measures, the period right around when Bear Stearns flatlined marked a capitulation of confidence and a crescendo of fear.

If yet another massive bank like Lehman came crashing down, the amount of uncertainty might be too much for the market to handle, causing another downward spiral of fear that could mean some serious trouble for market and consumer confidence. In what would normally be seen as a vote of confidence, a Barclays takeover might be seen as an attempt to save a bank that can't stand on its own.

What does Barclays see in Lehman?
With big bank stocks like Citigroup (NYSE: C), Bank of America (NYSE: BAC), and Wells Fargo (NYSE: WFC) all trading at or near five-year lows, it's clear investors have just about given up on financial stocks. Maybe these stocks are screaming bargains, or maybe investors are coming to terms with the fact that the sector's record profits were the result of a business environment we may never see again. Sure, if Barclays scooped Lehman up, questions regarding Lehman's ability to survive would end, but that doesn't mean it'll be all roses and daises from here on out. Lehman excelled on many fronts, but one of the big ones was the mortgage-backed bond industry that's since gone kaput. Regardless of who owns Lehman, those problems won't go away anytime soon.

It's quite a coin toss
Lehman's likely in one of two positions: It's either absurdly cheap, or it's on its way out. From that point of view, a buyout at anything near these prices could be a severe slap in the face, or one of the last remaining hopes.

For related Foolishness:

Fool contributor Morgan Housel doesn't own shares in any of the companies mentioned in this article. JPMorgan Chase and Bank of America are Motley Fool Income Investor recommendations. The Fool has a disclosure policy.