Very beautiful suburban area with lots of development happening in the area...well, last time I was there which was sometime last year.You've definitely come to the right place for your real estate investing career. 

Where it gets fuzzy is - how much does HUD (their software, to be exact) expects to get, for the bid to be accepted?

Your dilemma is exactly why I took my properties back and developed a software to simplify management so I can do it myself. 

You may also hire licensed contractors and sub contractors as the owner of the business/property.Not in Oregon you need a license to flip houses.. its called a developers license..

I'm a mid 20's software engineer by day, a platoon leader in the Army on the weekends (guard), and a FI/RE/investment enthusiast 24/7 (yes, I often dream about investments)!

If so, are there any areas to avoid or areas which are being developed?

With all these new developments there is also quite a large scale apartment development mid way through completion.

However, maybe I'm not thinking deeply enough.What other ways could investors approach a development of this size?

Chris Goff has some software that looks great as well REIPro. 

My primary job is land brokerage for new development, in fact I’m working on deals in your area: San Dimas, Glendora, etc.