Even if the property rented out at 1% ($4,000/mo net) I would be at a positive $100/mo.

Beyond that, my wife and I are semi-actively looking for multi family properties in the central Texas area and are also looking to acquire 1st/2nd position notes sometime in the next couple of months.

I am looking to put myself in the best position to succeed.

These types of debts become very personal in nature to the people on the board who are homeowners in the community, have probably spent a significant amount of money to try to get this collected, only to be in a position now of probably getting only 6 months of dues. 

If you have a lower gross rental income per bookings (say $150 average booking for a small condo) and a similar $20 cost per basket, but that basket includes nothing that is tied to the identity of the property or makes it unique, it seems likely the repeat booking rate and likelihood of positive review will have minimal impact.

He is in an upside down position, but the property can rent for $800, so even at $34,000 the deal makes sense.

My suggestion (after following Alina's) is to focus on saving as much as possible to put yourself in a position to invest and in the meantime it's education, education, education!

If there are other positives/negatives please let me know!

You'll need to run through quite a few agents to get one that takes this position, but it's the truth.

Pay attention to people , who mention both the negatives and positives .And while you save and build money , I would suggest you to build your emotional wealth as well , because  the whole investing is 75% mindset and 25% learning initially , once you do few deals it will become 90% mindset and 10% skills .Please also note that - while you do your research you will come across many many "gurus" , who are unethical and fraudulent .