This article is part of our Rising Star Portfolios series.

The short answer: I don't see any screaming buys. 

Don't get me wrong; I would love to kick off my Rising Star portfolio with a juicy fat pitch of a stock pick. What better way to ignite the portfolio than to put our money to work on day one?

The thing about fat pitches, though, is they don't come along very often. Charlie Munger, Warren Buffett's investing partner at Berkshire Hathaway (NYSE: BRK-B) (NYSE: BRK-A), claims that if you take away Berkshire's 15 best investments, their investment record will go from world-class to mediocre in a heartbeat. And they've been at it for more than 40 years. To be frank, I refuse to buy something less-than-stellar for the sake of timing it well with the portfolio's launch. I'm about making money for the long term -- optimal publication dates be damned.

But I almost bought ...
I have, however, come close to buying shares of Pebblebrook Investment Trust (NYSE: PEB). Pebblebrook is an investment vehicle formed for the express purpose of buying up hotels on the cheap. In the past six months, the pickings have been good. The economic downturn has wreaked havoc on the hotel business, and many heavily debt-laden hoteliers are being forced to sell their properties or risk defaulting on their loans. That's where Pebblebrook swoops in, buying hotels at fire-sale prices -- and usually without the debt. As it turns out, it's a lot easier to turn a profit in the hotel business when you aren't using all of your operating income to pay the interest on your loans.

Betting on the jockey
An investment in a vehicle like Pebblebrook is really an investment in the guy or gal making the investment decisions. Enter Jon Bortz.

Bortz is our jockey, and he has a track record of buying hotels on the cheap and turning them around operationally. After starting the hotel investment division at real estate firm Jones Lang Lasalle (NYSE: JLL), Bortz founded his own venture, LaSalle Hotel Properties (NYSE: LHO), and bought up 31 hotels over the course of a decade. Apparently, he couldn't pass up the deals he has been seeing lately because in the past 11 months he has come out of retirement, launched Pebblebrook, and already bought five prime-time hotels, including the Sir Francis Drake in San Francisco and Hotel Monaco in Washington, D.C.

Are the deals really that sweet?
The reason I'm unprepared to commit capital right now to Pebblebrook shares is that I'm not positive that Bortz is making out like a bandit on all his hotel deals.

Some of the deals look incredible. For example, Bortz bought the Intercontinental Buckhead in Atlanta for $105 million; by my calculations, the hotel is worth $115 million even if profits never grow again -- and considering how poorly the hotel has done the past couple of years, it is hard to bet that it won't generate more cash in future years.

But then there are deals like the one Pebblebrook made to buy the Sir Francis Drake. I have a hard time reconciling the $90 million price tag to the iconic hotel's earning power.

Don't get me wrong, Bortz can definitely be a savvy buyer. He bought the Doubletree Bethesda outside of Washington, D.C., for $67 million. This seemed like a break in protocol to me; Pebblebrook generally focuses on upscale hotels in major urban areas, and buying a chain hotel that happened to be in the same town as Pebblebrook's offices seemed fishy. Further digging, however, revealed that the Walter Reed Medical Center, the U.S. Army's flagship hospital, is being moved to Bethesda -- directly across the street from the Doubletree. The day the new medical center opens its doors, that hotel's occupancy struggles will be history.

What's next?
Pebblebrook certainly has potential as an investment. But before I buy stock, I need a better understanding of Bortz's modus operandi. He has the track record, and he's certainly been around the block. But still, I'm not about to put my, and, more importantly, your money in his hands on faith alone. For now, the jury is still out on Pebblebrook. When I reach a verdict, you'll hear from me straight away.

In the meantime, head to our discussion boards with your thoughts, questions, and comments on Pebblebrook Investment Trust.

This article is part of our Rising Star Portfolios series, where we give some of our most promising stock analysts cold, hard cash to manage on the Fool's behalf. We'd like you to track our performance and benefit from these real-money, real-time free stock picks. Click here to see all of our Rising Star analysts (and their portfolios).