OOS investing is much harder than it looks and picking a random city that you don't know much about will put you at a disadvantage. 2) Network with several local investors in the city you're considering investing in.

There are advantages and disadvantages to house-hacking which you will discover as you go.

All deals have their own unique structure and you should understand the advantage and disadvantage to taking distributions along the way vs. a higher payout of profits at the end.

Being 2000 miles puts me at a disadvantage to not be able to check on my Indiana properties. 

I was also thinking that this may lower our office building payment which is good for our personal cash flow with other investments moving forward.Thank you all for the advantages/disadvantages and I hope this doesn't come off as an irresponsible thought.Kegan

The disadvantage of living in NYC is that the prices of homes here are high.The advantage is that our salary is higher than other areas.I think you should consider to continue living in NYC and invest in out of state rentals.The only exception would be, if you can work remote and keep your NYC salary, then I would consider a house-hack elsewhere.

I can see the advantages of completing your own legal work (familiarity with your business, more attention/time/care, and saving money) but also the disadvantages (spending too much of your time completing legal work, too close/emotionally connected to the business, and not being an expert with residential leases).  

If you comp set is offering that amenity and you are not, then you are likely at a competitive disadvantage.

Now I think the only advantage of WL is its tax advantage ( for life insurance we can always buy a cheap term), disadvantages are cost and unexpected withdraw or cancel cost.

You're at a disadvantage.