On the eleventh day...The ride to the airport and back was a big help, thanks!

I grew up the old fashioned way, no dishwasher.

You can live in a more affordable place like Plymouth, Kingston, Pembroke, Carver, etc. and still have a relatively easy ride to work - not to mention that these areas are much less congested and have pretty low crime rates as compared to parts of Boston.For example, there are currently 68 duplexes on the market in Boston. 

You will likely need to ride out a potential recession so be prepared to hold much longer than 5 years.

When we started out we had our property manager collecting rents the old fashion way door to door. 

If it were me, I'd just ride her out until she passes away or goes into the hospital/nursing home.

My husband found it, during his morning bike-rides.

The buyer is likely just taking you for a ride.

So a properly written addendum that allows assignment of the contract would over-ride any clause in the main contract the prohibits assignment. 

Also building equity into your property is smart, especially if you can save money doing it yourself in a timely fashion.