This type of property has the chance to cashflow, even highly leveraged, in a market where cashflowing properties are quite difficult to find.Could house hacking a property like this work while I am going to school? 

Was this a difficult process, and who did you talk to in order to do this?

If you are not going to refinance (which may be difficult anyway since you don’t have a job), but are able to pull out HELOC I would use that money for short term investments such as flips or BrRRRs.

Conventional financing would be difficult as they typically require 12 months seasoning to use the newly appraised value.

Most municipalities have different mix-use categories which dictate the precise commercial use that's allowed.A few additional observations on mix-use assets and how I approach them (1) they are generally more difficult to finance than multi-family assets so expect lower leverage terms even if the property performs just as well if not better than a multi-family property and therefore price this into your acquisition (2) I focus on mix-use assets where at least 80% of the income is generated through the residential component.

I have noticed with all of the guru's out there, it's gotten more difficult.

Otherwise your financing will be difficult.  

Once I gave in and bought a few only to not have assistance and no clear direction so frustration took over and I was still learning but needed direction, I finally found a group of investors to help me,  guide me,  and teach me the ins and outs of the industry.If I am not working deals learning the ropes or watching videos for extra information in real estate investing you can find me at my full time career as a Auto Injury Claims Specialist with big red.

One perk with these companies is that they often extend the lease as construction timelines are notoriously difficult to estimate.

You can see how it works with each OTA, what limitations API has with each particular OTA, what it can and can't do, exactly, how difficult each of them are to set up, etc.I did the Hostaway call and they wouldn't really expand on any of this.