I'm a newbie but lived in NYC for the last 10 years, my wife all her life. What I'm seeing these days are headlines like "Bay Ridge is the new Park Slope". I live in BK now off the Q train. I can tell you development around here is happening and fast. Buying up dilapidated tiny homes between apt buildings to build small 7 to 8 floor rental units. I have two brand new brick windows because I'm living next to one of those developments :)
Up and coming from what I see is further down Ditmas Park/Flatbush into Midwood along the Q and border of East FlatBush along Flatbush Avenue. There is a fairly new Target and a brand spanking new Dallas BBQ. Blink Gym, Models, starbucks. Its still a bit flavorful in this area with recent robberies, and a murder in one of the houses off Cortelyou Rd (which is a trendy street). Of course rents are sky high as landlords catch on and charge accordingly.
I'm facing the same problems with Boston and high priced entry but lucky that my father invested in a few buildings in leather district back in the late 80s/early 90s and a house in Quincy for a flip/buy and hold. I'd love to get into buying and renovating a live in multi family but will just focus on the main buildings we own and try and increase their value and get different clients in them. The market is hot and I think will continue to stay hot. I'm not into condos but unless I venture way out I won't find anything that will cash flow. Multi families are hard to come by unless in Dorchester I feel. Quincy has talks about development and I think Malden has potential too. THese places are still developing but close to trains to Boston which is really key as driving into Boston is terrible.
Maybe I have to look into NH or western mass near Northampton which is a big college town. But prices there are expensive too. Whenever I hear on the podcast of houses going for under 80,000 or under 50,000 my jaw drops.