Probably Laguna Beach is a special pocket which is not influenced by crisis too much, so it does not matter when to buy.

Also put together a list of your "sphere of influence" people, all those you know, at least 100 people.

Use your circle of influence!

How do you approach people in your Sphere of Influence that do not live in your local area? 

Whatever fee you decide make sure is a substantial amount higher than the increase and I guarantee they will sign renewal.

Which you would be doing.Most likely, you'd have to give them substantial reason why the new fourplex would improve your quality of life.

(Plus, in Virginia, you'll probably have more permit requirements than I have here in Texas - you may have to get a structural engineer sign-off on any substantial changes.)Can you insure it cost-effectively?

If you study finance, you will see you can substantially boost your turns by borrowing at a cheaper WACC (weighted cost of capital).

The National Real Estate Investor (5/3, Anderson, 131K) reports that, according to JLL Managing Director John Manning, “CMBS has come back substantially and all CMBS lenders are quoting and actively chasing deals.”

So many factors influence cash flow:   your buy price, taxes, insurance, local rental pricing, PM (if applicable), maintenance, size of house, etc.