If you have kids, even better.

I had better luck with traditional business lines of credits with banks.

I am new to the Richmond area so don't know the Counties well - any suggestions on areas to look to find properties with better deal economics? 

Could have been done better How did you finance this deal?

The better your credit score and making sure the property is in an area that the lender thinks is in demand or at the very least is not declining or rural will help in potentially getting approved. 

I think New Hampshire is better for this type of rental business.

Always trying to make things simple, better, faster.  

Great quality work even better quality people to work with.

how do you determine if its better to put up a billboard yourself and just lease out the rights to an advertising company, any thoughts?

For the long hold, San Diego I likely to have the better cash flow potential (assuming you do not consistently extract cash out of the properties).