., some of which you mention, so it seems you must be aware of them.As an investor, your goal is typically  to maximize your return and minimize your risk.  

Does anyone have any ideas on how to minimize that tax liability and still continue with my original intent, or is my only option a 1031 (I'm aware of DST but don't see that as a great option).  

As for the value of carrying, I believe it's minimal.

Since this is a family property you likely know it inside and out during your ownership so it should minimize the number of calls you get and glitches in the unit.

I've spent the last year or so (on and off) looking for my first investment property to house hack but have had minimal luck.

We also use software to document/communicate out to ALL residents during the lease term in order to minimize inquiries from parents who aren't well informed.

Occasionally you will get no occupation which if they fill in an agency or other info is fine but you have to have minimal data.

What really bothers me is these so-called gurus are all using the same model... entice you with glitz and glamour of how you can become a "Real Estate Genius" by using there systems only to find out after you have paid thousands of dollars to them most of the info they teach can be found for free or at least minimal costs.  

You can purchase the first one with a private loan from your dad or cash to minimize risk, and leverage a second or third property with a bank loan and the rest of your cash.

If you are not a real estate professional and bonus depreciation is limited to 40% starting Jan 1, the tax benefits are going to be pretty minimal unless I am missing something.