You and your legal, tax and financial advisors should review this transaction in greater detail, especially the PLRs, to ensure you understand the significant risks involved and are structuring the transaction as close as possible to the PLRs to mitigate some of the risks.

I am not privy to their financial situation.

For the lease, can you list the girlfriend as an occupant rather than a co-tenant since she won’t be a financially responsible party?

Being a responsible person has nothing to do with the financial calculation for rate of return or cash flow. 

Ultimately, balancing your student debt and financial goals will help guide the best decision.Good luck!

Moving into REI is daunting, but everyone I've met so far has been amazing.

We've found it's more capable than others when it comes to integrations, reporting capabilities, and efficiencies.The software you've mentioned will be better for the PM activities (property-specific transactions) than keeping up with your financials as a whole. 

My goal is to have financial freedom so I can eventually quit my 9-5 job and use my time to spend with family and do things that excite me.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

While the initial years might not be financially lucrative, the knowledge and skills you acquire will be invaluable.