House Hacking in Boston

[Scott Jacobs]

I am looking to house hack in the greater Boston area by purchasing a two or three-family so we can house hack. My wife and I currently make 300k a year from our corporate jobs, but we would like to get into real estate investing. We have no debt and each of us has a credit score of 780+.  I just finished building out my investment property calculator in excel to run the numbers and I have read a few books (Rich Dad Poor Dad, The Book on Rental Property Investing, and Long Distance Real Estate Investing), but I wanted to get insight from people on what is the best strategy for the following questions below:

Where are the best areas to invest closer to the city? 

What percentage should we put down? (We expect to have 120k in cash saved up by EOY, not including other investments)

What is a jumbo loan? Is it a bad or a good thing?

Is now a good time to invest or should we wait a bit longer for prices to drop?

Where is the best place to look to find a mentor?

What other pieces of advice would you give us as we start our journey?