Here are some recommendations for you:Find and connect with other BP members that are in your area: http://www.biggerpockets.com/meetSet up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/alertsRead Beginner’s Guide: http://www.biggerpockets.com/real-estate-investingIf you wish to tag someone in the conversation on the forum, type @ followed by their name and then select the name of that person which should appear below the comments box.

We are also considering making an offer on a house that will be a live in rehab but will also be a conversion from a single family to a triplex. 

Any help to start the conversation is appreciated.

They either close or lose their EMD.For big projects, like condo conversions or apartment bldg. purchases, we do allow buyers an  inspection period clause in the contract.

Any advice on how to handle this conversation and what a potential lender is looking for would be great.

You don't know that, didn't let his gruff initial conversation run you off, and now you've had a nice chat with him again.I'd make it a point to call him every month or two, just to say hello.

We were discussing some of these same things over at:Zoning/ADU advice in Seattle on the BiggerPockets forumshttp://www.biggerpockets.com/forums/52/topics/396578-zoning-adu-advice-in-seattleYou may find the conversation and links helpful there.

It has helped my company quite a bit in the beginning to manage who we are talking to, what our last conversations were, sending out mass emails, etc.

Here are some recommendations for you:Find and connect with other BP members that are in your area: http://www.biggerpockets.com/meetRead Beginner’s Guide: http://www.biggerpockets.com/real-estate-investingCheck out BP Podcasts: http://www.biggerpockets.com/renewsblog/category/podcast/If you wish to tag someone in the conversation on the forum, type @ followed by their name and then select the name of that person which should appear below the comments box.

When it comes to structuring the deal, tell him you will give him his asking price but you need him to work with you on the other terms.things like "I'll give you enough money for down payment to show that I'm serious" is a good start for the conversation about the down payment.