I get around the country to most major metro areas were I work and invest and nothing frankly compares to the hospitality and SAFETY of Portland for this size of city..

I am already working with my wife to implement everything we can and get on the path to being a millionaire if not more! 

Through many conversations over the last 2 weeks with my wife we have decided to pursue the investing path.

Everyone in our country will be allowed to invest in private offerings with national exemptions and solicitation starting today.  

This week most of the country is red hot (it you are to read just the headlines) ... and just in-time for winter.

As of today, we have risen another 3% nationwide average since July 2015.The Midwest, from Wisconsin to Texas, are on the higher end of the price recovery, compared to other parts of the country, like East and West coast.I hope this helps you. :)

On the other hand, parlaying my existing equity into a portfolio of 3-5 cashflowing properties in the $100K range (with 20-25% down) in other parts of the country -- places like Memphis, KC, Charlotte, etc -- is attractive because if I get in with the right Turn Key companies I could use my cashflow to continue to acquire additional properties over time and leave the details to the professionals.Are there other strategies I should consider? 

I recommend you listen to the podcasts which can be found at www.biggerpockets.com/podcastsRead the beginner's guide, for which there is a video course version as well at www.bupainternational.com/courses These will get you started and help you choose your path. 

It is more related to how Hoboken and JC have and you think that area is next in line given the Path train and proximity to NYC?

If I choose the short-term rental path, I would want to find an excellent property manager who specializes in vacation rental.