depends what you want, I lived in the city center but Orchard area is very popular, I liked hanging out at Clarke Quay for drinks and around marina bay sands.
I am traveled all over Asia and yes there are sone great places out there but for me Singapore was never dull, I made a lot of local and expat friends so was always going out and loved it there. Now Pattaya is my home so all good
I lived and worked in Singapore for 10 years, far from dull!! It is expensive but lots of great restaurants and bars/clubs and shopping for high end luxury brands
Book direct with the airline or if you use an site like cheap flights, make sure all segments are with a code share airlines , then when you first check in the airline cba check you bag a the way through. If you use 2 different airlines that are not part of the same group the 1st airline will not be able to check.your luggage onto the next flight.
If you want to do a long layover book using multi city, it is very easy to have a night stop.over then carry on, I do this all the time.
Your only mistake was you were arriving and currently there is only a 30 day visa exempt entry so when you said 60 days, you don't qualify for the visa exempt so in principle you would need an actual visa to enter for 60 days. Yes it has been discussed the visa exempt will change to 60 days, we could see it July 1st but no official confirmation yet.