If you plan to self-manage, that helps, but you also need to consider the eventual sale (even if it is 20 years from now).  

I would like to start off house hacking and eventually work my way up to generating enough passive income to just relax a bit and enjoy my time with my son.

Starting out I'm looking for single family rentals and small multi-families, and will eventually scale up to some larger multi-family properties.

Eventually, I can use 1031 to get into MFU.Can anyone give examples of when they have done this?

But the more I grow and experience, I will eventually do more contributing then learning...and then when I take action on my first purchases and experiences, I will share as well.  

Do you guys think it might eventually expand to that area as well once all the other areas start getting too popular/expensive for renters?

My plan is to flip the house eventually, but how can I reach a deal where both of us can come out satisfied? 

I would love to offer some  assistance in the scheduling/coordination of your projects in exchange for your some of your time and expertise as I step into finding and eventually closing my first deal.

Both were deals that I had offered on multiple times over 5-6 weeks where continuous follow-up by my realtor allowed my offer to eventually migrate to the top of the pile when others decided they did not want it, or their home inspector freaked them out, or where the property did not meet FHA guidelines so it fell out of contract.Right now I focus on duplexes and triplexes where the rents are strong and improving.  

Because it is the Land that will eventually go up in value and you can make more Cash Flow with Boxes.