It’s more of an up and coming inner ring burb, tho still technically in the city.

I have multiple years of technical training and a decade of experience, but the company obviously does not value that.

I've been using the same insurance agency for many years, but they recently changed the company name and staffing. 

I currently hold their security deposit, only $500 and technically I have threatened to report their business to code enforcement before (I held off) but I could use that as a negotiating tactic for leaving on time, since the fines are up to $5000 in Miami and it’s possible this tenant Does not have full citizenship status. 

The technical language of the code section generally can be read to require management LLCs to obtain brokerage licenses.

It is far better if the landlord just lets Tina out of her lease, and accepts Sam as a new tenant.Or, the landlord might let Tina out of her lease, accept Sam as a new tenant, but also require Tina to guarantee Sam's lease for the final six months (using my example) of Tina's lease term.Either one of these accomplishes everybody's goals without getting into messy technicalities that come about with a sublease.Most leases contain prohibitions against subleasing without the landlord's consent.Many leases charge a one-time fee if the tenant subleases, or is let out of their lease and a new tenant accepted.That is because the situation causes extra work and risk for the landlord. 

You can technically avoid the issue if you pick a contractor that's incorporated.

@Christopher Veljkovic  Technically I am waiting to move back to Indianapolis to invest in order to house hack my first investment. 

From a technical perspective I also run into a lot of investors that: 1) Don't understand the basics of title, transfer, assignments, endorsements, deeds etc.

2nd for delaying closing until after the place is vacant... however you technically would be in breech of contract and seller could nix the deal and have a claim to your EMD.