Lets put the shoe on the other foot what if it was your property would you want to be lied to. 

NOW Let put the shoe on the other foot and see how it fits...Lets say you are a seller (which if you are an investor you will be a seller at some point) and you decide to or need to sell one of your properties so you contact the best agent in the area and ask them what your property is worth in the current market. ( by doing so you have established a fiduciary relationship with the agent. a relationship of  the highest trust)  The agent says that its worth 50,000 and you sign a listing agreement.  

The shoes are gone so time to save the watches......... : )You need to run a rental business LIKE a business.

If I were in your shoes, I'd look for a 3-4 unit with what I call a great "Owner's Unit" (a unit that is much nicer than the other units, maybe with a garage, extra bathroom, more bedrooms, dining room, separate heating, etc.)My two cents...I am almost done my first RE investment book which has a chapter running the numbers (very VERY "BP'ishly") for doing just what you're thinking, using 2,3 and 4 units.

I've read your post and I feel, that I'm in the same shoe as you are.

The buyer puts the contract into escrow as he has now stepped into your shoes via the assignment.

Am I too goody two shoes for the modern real estate world?

Tim, I agree with most of what you said, but put yourself in my shoes and someone you trusted (a friend) told you one thing but did another.

This seems contradictory since I am essentially trying to do the same thing as a would-be purchaser, that is, buying a renovated property and financing it with a mortgage (the only difference being that I already own it outright) This new loan officer said the reason the seasoning period is different is because lenders are afraid that someone in my shoes could potentially walk away from the house once 80% of the cash was taken out of it, and the would-be purchaser has more of an incentive to actually keep the property.

Basically for all my trial and error (and sitting in your shoes as a one man show fielding about 10 to 60 phone calls a day) I found that I'll NEVER eliminate the calls, only figure out better ways to handle them.