Only problem is I’ll be newly married and my wife won’t want to move more than a couple times and absolutely no room mates in the same direct area.Or I could use my savings to find the right deal to live in flip and house hack for 2 years to hopefully multiply the month put in?

There's a ton of options, you could always house hack a regular SFH with roommates from work and then if you leave you could keep it going like that or sell it if that seems like a better deal.

With SFH, do you plan on getting roommates and rent out the rooms?

The biggest concern I have moving forward is effective management as a landlord/my own tenant and choosing roommates who won't make me want to rip my hair out!

.- For buying my first multifamily buy and hold, how would I go about buying it so that the house is ready for me and my roommate to move in back from deployment and have people live in?

My tenant’s lease is up and he’s going to need a new roommate for the two bedroom.

So without great credit his mom couldn't buy a house, so he bought a townhouse in his name and then invited him mom to be a roommate and pay the same amount she was paying at the rental townhouse and they got one more roommate and now he's still living for free, with his mom as his tenant. 

That would typically not result in an apportioning of space since the walls and spaces are all common and commonly used - just like house hacking with roommates.  

After a little over a year of sharing space, we realized that we're just not great at being roommates so I'm looking to move out. 

Other areas to consider that are not directly on the T but close would be Everett and Chelsea.2 BD certainly has a high demand, since it can be used for a young couple, young family, or roommates, so its very diverse in terms of customer range.