People coming to the mountains to hike.

To me, being financially free would to be able to work a more flexible schedule, be on the boat on days when I would typically be at work or on the mountain on mid-week powder days! 

Generally you want to pick as table or growing city.

If you go with $1,150 and the market is between $1,300 - $1,400, you are leaving $3,600 - $6,000 per year on the table.

I am the other side of the coin and could manage to qualify but need to bring 20% cash to the table and have entertained a hard money lender on a 1 year term before refinancing and paying out the lender. 

The chips you put in to losing hands, are not lost...they're just in a different pile on the table. 

If it doesn't appraise for the asking amount, then basically I would have to bring the difference to the table, or walk from the deal, right?

Or is there another way to offer that still leaves negotiation on the table?

As Aaron mentioned, each agent is going to bring something different to the table and I would suggest being very honest with yourself when it comes to what you are good and bad at.

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