After selling the property, I discovered it would actually be 2 to 7 years before I would be able to obtain another loan or refinance (not happy).I sold the home because I did not see the property ever reaching it's 2005 value ($172,000) and the $430 a month shortage drove home the fact that I was throwing money away.  

I am in an extreme shortage of buyers, that's my dilemma.  

There is definitely a shortage of affordable rentals in this city.   

Above all, stay positive and remember "there is no shortage of success" (Grant Cardone)

Tons of places (including my area) have a shortage of affordable housing - so start there and then, if I were in your situation, I would look at places where the cost to acquire is relatively low.

I imagine that there will be no shortage of tenants in lower income working class neighborhoods that are close to jobs and schools.

@James SwiftInteresting, I didn't realize there was much of a housing shortage in Salem.

However, there may be some good opportunities in spec builds (especially under $300K) given the extreme inventory shortage of SFRs we currently have along with a good supply of vacant land/undeveloped lots in the surrounding areas.Also, check out the CRIEA club if you haven't already.  

I have a lot of other older friends who see real estate as the means to fill in the gaps/shortages as the plan or live their retirement years out.  

Rochester right now is experiencing a shortage in supply because less people want to sell their rentals since they are increasing in value.