Getting to know the Boston Market in 2015/2016

[Chelsie Librun]

Hello,

I'm looking to get into the Boston market through buy and hold and renting for cash flow. Yes I know it's difficult, but if there's a will there's a way.

After graduating from school in Cambridge, I've lived in Roxbury (near Jackson Square), Mission Hill, and now Savin Hill in Dorchester. I have a couple friends who have bought houses in Fort Hill in Roxbury and Savin Hill, and are making good cash flow, but this was back in 2013, and I don't know if I've already missed that wave.

Question is: what areas in greater Boston are best to look into right now? Currently I'm thinking of looking South (Dorchester, Milton). I'm also into looking into the North Shore (Andover, Lowell). I currently work in Tewksbury, so managing a property up there would not be too difficult.

Please let me know your thoughts. I feel like as the winter is coming (cue GoT theme song), the market will slow down just a little bit. I'm willing to trudge through the snow for a good deal.

Chelsie