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 .

When I worked in Corporate America and a position opened up, the manager would always ask "who do you know" before advertising the job publicly (80% of the job market is "hidden" this way).

Also, if a home was purchased and "Brrred" then the property could be sold to the child at a below market price (with the 7% interest built into the price) putting them in a position that PMI might not be an issue due to the equity built in from the renovation. 

He qualified with income but only due to lots of overtime and gave me this story that he has an interview for a Sheriff position in a month (never happened).  

We hope to be ready and in a position to start making moves within the next month or so.