First off, I disagree with the idea of too old to have roomates: You do what ya gotta do to make money and buy a place.
I think you sights might be set too high. A cursury view of realtor.com shows lots of Condos for sale in Berkeley for under $400,000. (2bd/2bth). Buy something like this. (never sale any of your realestate). This would be a nice starter place for a single guy. Rent the other bedroom out. Not the most desireable thing, but hey, someone else is helping you pay for your first place. In five years take some to the equity out an move up. Rent both bedrooms out.
I did this and now have one condo, three rental homes and my current residence.
First place wasn't much to speak of, but a few home depot classes go a long way. As long as the building location is fairly good.
PS. You don't need to make six figures to make this happen.
555 PIERCE ST
ALBANY, CA 94706
MLS ID#: 40243550
$398,000
2 Bed, 2 Bath
1,040 Sq. Ft.
Estimated payment:
$2,013 Per Month