If anyone has had a similar experience, I would love to hear about how you tackled this obstacle!

That will eventually need to be fixed, but it’s something I can tackle using the profits from the property or a line of credit secured by the equity in the property.

Remember, your rate of return on paying down the debt is guaranteed (unlike any other investment)... that is assuming there is no early payment penalty, which most student loans should not have.Here's an article about a good friend of mine and how he got serious about tackling student debt.

Not too long after we were ripping out the vanity and flooring and then I tackled the other bathroom on my own.

If you can tackle bigger portfolios you can knock down prices more so then on single one off units...

I eventually settled with my roofer who did a pretty decent job on the roof, to help me to GC the project and promised he could tackle it within my budget.

QBI is one of the most complicated stuffs, so don’t tackle it yourself. 

Automation only takes you so far and in my opinion once you get over 10 units, it takes two people or a VA and owner to tackle all the guest messages ( in my humble and personnel opinion) unless you really like exchanging messages with guests.  

Would either of you mind sharing the lender you found that would tackle delayed financing?

If I were you, however, I will tackle that 40K student loan a little faster so as to start putting money aside to cover Cap Ex or major capital improvements on the property.