I am 29, like long walks on the beach, fly fishing, and rehabbing homes in the Twin Cities.

@Matt Fish, your second last sentence starts "#2 requires less renovations

You may be fishing for opportunities to slice off a few thousand, perhaps more, without risking your own money or credit. 

Paddling, barbecuing, learning to fly fish currently, and Im currently reading about aquaponics.

In my business (technology) we are often passing clients with smaller budgets down to smaller fish: freelancers, college students even.By doing this, over the longterm, you are building out the same investor network that could help you start your own REIT.

is this something where i really need to fish and poke at them a little bit to see if they will keep going lower?

Is he motivated to sell or is he just fishing?

Fly Fishing Guide

For the fish that do bite expect Trailer Park full of sex offenders with pit bulls sitting next to the car on blocks, adjacent to the failing Lagoon.In most cases you're just going to anger people by giving them a letter with a good price to find out they fit the scenario above and you're overpaying, or anger them because you're way under and they won't even contact you.This is why people don't do it.  

I'm like a fish out of water with seeking my first flip.