We as a firm have investors working with us who have rental properties all over the US big and small.Finding a real estate-focused tax professional and one who can help with advisory and grow with you would be my suggestion to focus your efforts on finding.

If the numbers don't work for developing new construction building of that scale - what path do you suggest I explore in order to get the most benefit from land? 

My dad suggested I use a PM, but I'm going to see how I do self managing. 

How many years would you suggest working a job after college to make the process of getting a househacking property every year easier?

But I wonder if I am missing something.

I really appreciate your recommendation and will probably move forward with something similar to what you have suggested.

However, difficulties aside, you have to learn how to source cheap houses (I suggest off-market) and renovate.  

Any suggestions would be appreciated. - Chris 

Just a suggestion, it could be that for something which feels a bit more temporary/shorter time warrants a bit more flexibility from a screening standpoint. 

I would suggest that you look for some local meetup groups in your area.