I do commercial only but learned some of these tips when I went to conference and talked with an older couple that had listed high end homes for 20 years.Good luck.     

Talk to him about your thoughts including the fact that you are not trying to step all over him.

2) When people talk about putting a house under contract, does this mean they've put an offer in with contingency, or is this some form of creative financing?

Talk to your lawyer, who will probably talk you out of this.

You don't necessarily need to talk to the listing agent. 

I have heard people talk about finding an an investing "edge", and I think trying to retrofit buildings to a passive house standard may be a good one.What do you think about the idea of buying a house that needs to be renovated - perhaps gut renovated - and fixing it for rental to passive house standards (or as close to that as possible).If the cost is equal or less than renovating a house to current code standards, then it would follow that renting that house would provide a better return on investment.

What DF did to investors is put us into a box of "preditor lenders" that DTI and 1003 and ATR ability to repay is the regs attempt to force us to prove this loan is NOT preditory, is affordable and a good value.A lesser talked about need is to show that selling price is "market value" and not a picked out of thin air price the investor picked to their advantage.  

@Len Roche my first loan was with Wells Fargo (back in 2009) then I talked to my brother-in-law about a loan he had on his investment property with American Airlines Credit Union.

Happy to talk you anytime.

@Brandon Smith That makes sense, I will talk to the conventional banks that I am currently dealing with.