Considering the neighborhood and size of the house - the two most important factors in the ultimate value of the house - and using comps and my knowledge of the local market, I figure out a "drop-dead" offer, a likely offer, and a "fire sale" offer.

If you haven't yet, be sure to check out the The Ultimate Beginner's Guide to Real Estate Investing and don't forget to set up your Keyword Alerts!

Our ultimate goal is to have enough passive cash flow from real estate to replace our earned income which is about $15,000/month. 

I would ultimately like to be a real estate investor.

@James SchoenI'd suggest starting with the Ultimate Beginner's Guide to figure out exactly what kind of investing you want to do.https://www.biggerpockets.com/real-estate-investin...Once you know what you want to do (meaning you chose ONE strategy), then listen to BP podcasts where that investing strategy is the subject. 

Fill in the foundation below.Check out the Start Here page http://www.biggerpockets.com/starthere Check out BiggerPockets Ultimate Beginner's Guide - A fantastic free book that walks through many of the key topics of real estate investing.Check out the free BiggerPockets Podcast - A weekly podcast with interviews and a ton of great advice.

And what's ultimately the pitch to a seller?

My ultimate goal is to build up a large portfolio multi-unit properties and vacation rentals.  

Dumb question perhaps, but it's like paralysis by choices (a bit different I think than paralysis by analysis)

Ultimately the choice is yours, you have gut instincts and have met them... a poll on bp might not be the best business decision :)