It typically takes years to really establish yourself in the commercial real estate brokerage business, so you'll have be comfortable with that if you choose that route.If money is no object, both will provide good learning experiences. 

One currently has a family with a child in it.

That's just our comfort level as very small, starting out noobs.

Like I said, I've been doing tons of research everyday, just trying to get comfortable with terminology and basic knowledge, but at some point I need to just create an actionable plan and actually get my feet wet.I am also considering doing house hacking as well.

Once I had it narrowed down to 2-3 locations, I would focus on finding someone that you feel comfortable working with.

If those items have had been updated recently then you may be more comfortable with the Actual Cash Value policy for now and can look at a replacement cost policy down the road. 

The only hitch is getting the sellers or buyers to be comfortable with that process.

If you and your family can afford to still live as comfortably as you need to in the worst case scenario, then factor that into your decision and move on to the next point.

Another option is refinancing with the lower rates (when they reach prime) and putting some of that cash into the market - that is if the refinance still allows you to cash flow comfortably. 

@Tracy Munger @Sameer Bhalesha I've seen investors lock down inventory in my market because the purchase price is so approachable and they're taking a lot of comfort in section 8.