Firstly, I would never recommend anyone to get the Entrepass - best thing to do is just to register a business and apply for an EP pass as an employee of said company. Admittedly in this scenario you would need a local director - but services for this shouldn't run over $1000/annum.
The next statement about spending $100,000+ per year, is again - not true if you are on the standard EP pass.
Rents for accomodation are, however as you stated expensive, we're currently paying $5400 SGD / month for a 3 bdroom in a nice condo in central Singapore.
However, for 2800-3500 / month you can find 3-4 bedroom places that are lacking condo facilities but are more than suitable for living.
If you have any additional questions or queries please don't hesitate.
Also, don't take this as a glowing endorsement of SG - there are plenty of downsides to this island nation for tech.
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