House hacking in greater Boston is a good way to break in to the market.

We are buying our first house, We are using a mix of the live in flip, and house hack strategy.

For five years I’ve house hacked a short term rental with great success.

You can sell the condo on your way to Portland or probably rent it at a profit.Renting out the second bedroom (ie, house hacking) will definitely help the numbers!

Stuart gave excellent advice which is a great way to house hack a multi fam property. 

Then once that is done I’d like to house hack the home.

I include that to convey that I am very willing to take risks/live uncomfortably for a prolonged time if it means setting myself up to avoid a desk 9-5 as much as possible.The question:I am looking at buying a 3-4 unit (largest I can) multi-family and house-hacking.

For a house hack, I've read that it doesn't make much sense to have it under an LLC.

Or get a 3-5% conventional loan to buy a SFH and house hack buying every year while building enough equity to get into bigger deals.

I recently finished an awesome house hack and am hoping to finish strong with a HELOC to let me continue investing.