I did have another thought which was to try to find a multi unit ASAP around 75k, maybe a distress sale that is already rented and try to live off the income and leverage that if things take too long with part 2.My wife is 'risk adverse' to put it mildly and is very nervous, I am too really.  

Here in Western WA, we don't need air conditioning and our winters are mild.

@Christian LautenschlegerIt sounds like you have a mild case of analysis paralysis.

I had a mild interest in flying when I was younger and my ridealong experience wasn't much different so I quit that path.

If you provide something with a property, you're stuck repairing or replacing it.While only one state that I know (Arizona) of requires A/C if you *don't* provide it upfront (you did), you're stuck repairing it since it came with the property.That's why some landlords prefer to remove *everything* they can from a rental so they don't have to repair it if it breaks: washer/dryer, ceiling fans, window A/C units in mild climates, garage doors, pools, fireplaces, dishwashers, disposals, and anything else that can break.

But will it be mild?  

Love the sun and true mild winter vs. snow and bitter cold. 

Or is your area fairly mild temperature wise all year round?

After listening to the podcasts, reading The Book on Rental Property Investing (and a few others =]) and lurking in the forums for a while, I started to get more serious about looking for properties in need of mild to moderate renovations in Pittsburgh (B properties in A neighborhoods).  

If anyone has a process they use, please share.I am looking for strong cash flow markets that are well priced and will experience mild appreciate over the years.