But yes, I’m looking to house hack until I’m out of college with the intent of living rent free, with any extra cash flow as a positive.

If so, then send a letter a few months before renewal with the updated terms and given them an intent to renew deadline.  

If you had hired a licensed contractor yourself and the same thing happened you most likely would not be able to sue unless you could prove that the contractor was acting out of malice or intention to hurt your business but a recommendation or opinion on construction/repair/maintenance issues from a licensed contractor is very much within their scope even if it may be wrong but still follows code and other laws, it is within their scope and different contractors will have different opinions which is why they need to be licensed.  

Once you generate enough income through passive investments, you can then pivot from your full time job, if that was your intentions from the beginning. 

As @Wayne Brooks stated- a 1031 is doable within a few months, particularly if you can show that your intent was to use as a STR and not just a flip.

That is definitely my intention if all goes well

Should I be reaching out to the realtor simply to ask what the estimated rehab cost is even though I have no intentions to purchase?

The intent is to get a cash out re-fi in Feb 2020 after remodel is 100%. 

I've also heard from a mentor that a few companies up in the DC area are buying up land in the greenbrier area with the intent to turn the into Resort/Tourist locations so maybe they are thinking long term and a completely different direction than Multifamily/Commerical investments?

However 1031 won't be available for you until you purchase a property with the intent of holding.