Face to face is great. 

I tend to deal with the smaller banks where I can walk into the office and deal face to face; I think the personal contact is important. 

The Dilemma I face is this: My price range is $275k - $350k, but I struggle to find something nice enough to want to live in, that would also cash flow once we move again, turning the home into rental #3.

The biggest issue I see other investors face is trying to purchase the lot and placing a multifamily on it.

The biggest obstacle you'll face is finding a market where this is viable, and finding a good, reliable contractor.

This is impossible to answer without knowing what you have and what problems you face. I

Some of these problems are relatively minor (tenants complaining about the pet's fur on the furniture), and some could be major (the pet attacking a tenant), but all of them make your job as the landlord more difficult.When househacking, one of the TOP issues you'll face is preventing housemate disputes (I could write a whole book on that topic!)

Ask for the permit history. and if they will not do it over the phone (but they usually do), then you need to go down to the Building Dept and do it face-to-face....I don't trust my agent :) By the way, can you let me know what can be happen if we rent out mobile house which has non-permitted room?

With all of the new requirements that retail mortgage business's face, I just don't think RMLO's ever get a chance to develop the same type of skills as an underwriter all that often.  

I keep delaying the time that I plan to leave my job for real estate investing.The fear I face is a "catastrophic event" playing out in my head where I then have to deal with every obstacle put in my way to purchasing real estate.