After house hacking the 3-4 unit for 3 years, I intend to pull out what equity I can, along with the cash savings from my W2 and cash flow from my SFH (which will increase to $500 a month after I move out) to buy a larger commercial property.Any advice or input would be greatly appreciated!

I invest in C properties and some units are left just as nice as the tenant(s) entered them and some are a wreck (my one-bedroom apartments tend to stay in the best shape - larger properties with kids typically get wrecked to some degree). 

If so or if not did you see any negatives against using two smaller units in a room versus just one larger?

The more rentals you have the larger reserve you need to keep.

The risk is that, if this doesn't occur in time, the market itself will "sort out" the issues on its own and arrive at an equilibrium that is far from what most (or all) stakeholders would prefer.

If it's a larger organization, feel free to inquire about their different staff qualifications.2.

Two or so years down the line, the patch will start flapping in the wind again and the leak will start right back up.This is the sort of thing that if you don't have someone who's good and conscientious about small roofing repairs, and they are few and far between in this game, you're much better off handling it yourself, and if you can't handle it yourself, you're doomed to pay for the whole roof replacement anyway.

At that point I would think it would make sense to jump to larger buildings where you can get the economies of scale as well as better financing options. 

I think it’s easy to say, after the fact of owning rentals, starting off with flips or larger multis is the best route.

The more rental demand, the more government will try to tell you what you can do with your property and those laws are almost always in favor of the Tenant.This may be a good time to sell and get out of the larger metros and invest in the mid-west or other more conservative markets.