I’m currently employed full-time at a large software company and highly regarded amongst my peers.Although software is one my great passions, my desire for financial freedom is greater and grows with each passing day.

While I would say you're on the right track with your desire to invest out of state (Seattle really is pricey at the moment, like the new SF) I wouldn't get locked into investing somewhere just because you know people there or can travel there easily.

I can empathize with your desires to build speaking and writing skills.

Someone interested in the old NE style will not have an issue on desirability.

Just remember, no matter what business you go into, find out what KPIs you have to follow and NEVER let them out of your sight :)Also, knowing what to expect from each wholesale campaign will allow you to create projections for profits and let you know what to invest in order to get the desired returns.  

In the end, we had three parties in the same weekend that were interested so we actually got to choose the tenant with the most desirable tenant credentials.

I am realistic about prices in these neighborhoods, but still desire a minimum of $100 in cash flow per unit when I eventually move out.  

Some options to consider might be owner financing or lease option.I would still make an offer to wholesale, and gauge her reaction.If you don't have the cash for owner financing, and must wholesale or nothing at all, I would call her in a month or two to gauge her desire to sell.In my opinion, she would like to sell, but she doesn't feel like she must sell.  

I would still want something in writing if possible but all things considered if the above is true then yes, this is a much more desirable and I can see value here.  

Any repairs or clogs during the lease are the responsibility of the tenant.Wouldn't that take the potential economic risk off the landlord while giving the tenant something many desire?