Anyone in the DC area? What can I afford? Wait?

[Anon Guy]

Hi all,

I currently live in the DC area and rent in Arlington, but would like to eventually own / rent some real estate.  Unfortunately property values out here are outrageous, so I'd like to ideally find something in a gentrifying area that's a bit more affordable.

About me: 

• Age 34, single, but would like to settle/have kids within the next 5 years
• Current income:  115k.  Have enough savings to cover most reasonable 20% down payments.
• Excellent credit
• Currently renting

Ideal property:

• Somewhere near a neighborhood in an up and coming area that's not insanely expensive
• Metro within 20min walk or so (might be able to pass on this)
• Do NOT want to live in suburban hell
• 2 bedrooms so I could rent a bedroom out

Reasons I'd like to buy:

• Tired of paying rent (Though my share with a roommate right now is only $900)
• Believe that DC area property values will be maintained/appreciate given the location, employment rates, and shift of market bond money -> real estate

Reasons I shouldn't buy/maybe should wait: (there are a lot)

• Very indecisive on career - which means as I job hunt I could eventually change cities.  However, I've been like this for 10 years.  I figure if I leave I could always rent it out, though.
• Have only been at current job approximately 10 months, so this may impact lending ability
• At my age, I imagine I'll eventually need more space for kids/etc, though I suppose that's quite a ways off.  In 5-6 years I could rent out the place instead
• Considering going back for a masters degree, but that could be a very large student loan which would impact my ability to pay mortgage (or cut into 401k).

Thoughts overall?  What could I afford?  Should I just keep waiting?  But then wait for what?  I'm somewhat indecisive across my entire life right now (career is the main driver).