If you can get creative and make an area like Nanaimo work, I think it will be more beneficial in the long run especially if you can buy in the path of gentrification or transportation (South end of Nanaimo towards airport).

We were staying in Revere Beach, just outside of Boston. 

Generally speaking, with current rates, cashflowing will be tough anywhere unless you're purchasing something that needs work or that is a multifamily (even multifamilies purchased today are unlikely to cashflow where I am - Greater Boston)

I am new to the RE investment world, but working on getting started ASAP in the Boston, MA area.

@Jeremy Pace I do know many people who are 100% up front and do either offer to pay more than what the rent is, give a percentage or sign a longer lease than asked for.I plan on offering the same.I currently live in Somerville and most of my business is in the Somerville, Cambridge, Boston area.

What part of Boston are you from?

Investment Info:Small multi-family (2-4 units) fix & flip investment in East Boston.

Hi BP community,For those familiar with the Boston area, I was wondering if any areas outside of downtown Boston make sense to do air bnb / str's?

Also, isn’t Massachusetts heavily restricted on who can rent STR in the Boston area?

I'm located in the Boston area (Somerville, MA) Endless thanks!