Just Outside Boston Investing: Live In Multi Family. Opportunities realistic and affordable?

[Account Closed]

From what it seems big city investing is tough especially starting out and having no to low money. I am considering partnering up with my father to purchase a multi family live in home to get going with my personal portfolio. I have a deal right now just to live in the families current residential in downtown Boston, learning the ropes of property management as my day job. I know that is taking away some cash flow. I'd eventually transition out to a private property to raise my family (I need a yard for my baby girl) but would like to have it as an investment as well. Part of me sees the cons of a multi family is lack of privacy and dealing with tenants, but I figure if my ducks are in line and I screen properly I can just have cash flow on the side, my own place to live, and then help manage the property in town. Eventually leave the multi family for a bigger place and maybe sell it down the line. Not really sure how many years this plan would be. Anyone have suggestions or realistic time line?  Personally want to move out to the boonies few hours from Boston with land and a cob house and large garden and some sort of retreat center, and manage from afar taking over the family business and having my own multi family to manage. I'd like to delegate to property managers or live in property manager so I have more time to spend doing my other ventures with my wife. I'm just throwing out a number of a 10 to 15 year timeline estimate if all goes well. Any thoughts and is this too ambitious. I feel I just want to start somewhere build up and then delegate work after it stabilizes to have more free time. 

Cheers, 

Justin