Are there any markets outside Boston that any of you have had success with a house hack or tips to succeed in this type of market?

One that is pretty dang reliable for performance.

These minor details are the kind that distract people from the path of success. 

Quote from @Michael Smythe: Besides MANY self-labeled "gurus" exaggerating their success, many of them just supply readily available info.If you're too busy to find the info and are willing to pay for it, no problem as you accept their time vs money solution.REGARDING S8 GURU ISSUES SPECIFICALLYMost of them don't share all the facts about how Section 8 actually works.They claim you can get HIGHER rent from S8 tenants vs private-paying tenants.Why would the government allow our tax dollars to be spent this way?

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator – and they often select the first PMC they call!

though everyone at the closing could not believe that I was only 19 years old and buying their first duplex it made me feel really special and and good knowing I was performing better than anyone near my age group.

The Cape Coral Code Compliance officer showed the roofer the various emails to BTC, which left the roofer very unhappy as he then knew he had been misled and made him liable for a fine for illegally performing work while a red stop work order was in place.BTC appears to be continuing to cause damage to customers and other contractors. 

The success rate is below 30% so it is always do some arrangements with the tenant or move on depending on the case.

But always remember that RE is a risky venture, and you could go through years of less than stellar performance.

Building Strong Relationships: The Key to Property Management SuccessIn property management, success isn’t just about managing properties—it’s about managing relationships.