I would say all challenges can be overcome, and as long as he has a legal right to live and rent here (a pass at minimum LTVP) then all obstacle can be sorted.
The main question is why would you want to?
Spending a few weeks in an AirBnB looking for a place that suits your needs, where the location is good and where the photos match the actual unit would be more important. You can always offer a lower than asking rate which would more than save the AirBnB cost over the rental. You can negotiate to have the unit cleaned or something replaced, you can document anything faulty so you don't have to pay for it on the way out, etc.
And to see if the rental is reasonable, google URA rental
condo history and see the actual transaction prices not the asking price.
https://www.ura.gov.sg/realEstateIIWeb/ ... rch.action