It left a lot to be desired.  

Most of the small MFH (2-4 units) I've come across in SA has been in less-than-desirable areas. 

You would just need to do your Due Diligence so that you are able to see the potential in areas that may not be the most desirable at the moment.

Great to see you've found your desire for real estate.  

Congrats on landing the 2 flips in South Windsor and Simsbury, 2 very desirable places to live.

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.