I recognize the simple answer is talk to a REI friendly CPA (which I plan to do), but I'm curious what others have deducted to less their own tax bill if they just acquire a couple LTRs over time. 

I suggest you educate yourself on the options available to tenants - and what the coverages are. 

I haven't seen that model but it looks like its a simple IRR calculation over the 1,3 and 5 year hold periods. 

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?

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

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

Any suggestions would be appreciated. - Chris