I'm an agent in Boston in a similar position as you,  looking to pull the trigger on a multifamily.One other option you may also want to look into as far as financing  is concerned is the Mass Housing loan.Good luck and I look forward to seeing you around! 

Pull the trigger and ride it all the way through. 

The better you know your area the better you will know whether to pull the trigger or walk away.

Its a lot of work for the agent, but we use him so much and he gets a lot of commissions from us that he knows we are worth it.If you are earnestly looking to buy and you know you will pull the trigger if you find the right deal a good agent will understand and not get frustrated.

I would like to hear not only what the seasoned veterans have to say about this topic along with their stories, but also the wannabe investors who can't seem to pull the trigger and or did pull the trigger too soon.

I have been wanting to get my Broker's License for a long time but I have yet to pull the trigger.  

I heard that when an out of state owner sells a property in New Jersey that it triggers a 2% transaction fee.  

Your CPA can direct you on how to add your friend as a member and in what form so as to not trigger a gain recognition and satisfy their desire for ownership/cashflow.

Be careful though, depends on your state, but you might trigger doc stamps or other transfer taxes by deeding into a separate entity.

Selling would trigger capital gains and depreciation recapture (15% and 25% tax, respectively) unless you lived there for 2 of the last 5 years.