Not a good approach. Better is research what you enjoy looking at and/or photographing most, what kind of skies you will be mainly under, how motivated/serious you think you will be in this hobby, THEN select the best aperture size, focal ratio to fit those preferences.
(2) But as I read through articles on this forum for the usage of Orion XT8 and other telescopes I am now wondering if I should go for them first before Nexstar.
Same reply as in (1). Answer those questions to the best of your ability and you can come to a conclusion whether XT8 or other scope will be suitable for your next upgrade.
(3) I guess, the only way is to keep reading and asking / attending some stargazing sessions till I understand the basics a bit more better.
Totally agree. Try books like Backyard Astronomer's Guide and Star Ware. More efficient use of research time reading info already gathering in one book than hunting for bits and pieces of info all over the net.
(4) - Do you intend to use this 8" mainly at home or places very nearby?
Yes I stay across bedok reservoir, so around my home and probably some times at ecp.
If I remember correctly, the Bedok Reservoir area does not have many nearby shelter. Something to take note of and make contingency plans for. In the event of a sudden downpour, you may not be able to carry the whole 8SE setup to the nearest road to hail a cab.
(5) - Do you enjoy learning and doing collimation of a SCT? (not every difficult especially with Bob Knobs 3rd-party accessory)
I enjoy doing the focus / alignment on my beginer one (makes me feel a tad bit nerdy), never tried it on SCT , so not sure of that. But from what I have read, it can be a frustrating task.
With proper knowledge and tools, it need not be a frustrating task - e.g. basic understanding of star testing, bob knobs for SCT, laser collimators for Newt/Dobs. Newtonians requires most steps in the collimation and SCTs lesser.
(6) - Do you have private transport?
No mostly cab.
This can be very costly in the mid to long term. The money saved from not needing to do so can buy some good accessories or perhaps even another scope. Best is if you have friend who has a vehicle and can share you interest and staying around your area. Else, do consider something more portable and take public transport or walk to your ob spot.
(7)- Do you have a good view of the sky near your house?
I stay opposite bedok reservoir so thats where i usually go
If you have a good view from within your house, you will be able to make use of a bulky 8SE more and thus can justify better upgrading to it and occasionally bringing it out for major events.
(8) - What is your rough budget and have you considered other scope design options like a Maksutov and Dobsonian reflectors that may give you better performance on the same budget?
I am ok upto 2-2.5k for a computerised telescope, I recently read more on OrionXT8i and wondering if its easier to transport? I am very open at the moment, Nex star 8se or Lx90 (80) seemed like good scopes to compare against so I started looking at them and now catching more info around other scopes.
Portability wise, dobsonians generally are most bulky. But if you have budget, there are special dobs designed for portability in mind. Throwing another question here. Do you really need a computerised mount since you are not really into astrophotography yet? If not, the savings from a getting a cheaper non-computerised mount can be used to find a bigger aperture scope or buy better accessories to enjoy the full potential of the scope. But 2 to 2.5k is also a decent budget for used scopes so do continue to monitor the astro forums buy sell section here and in CloudyNights and Astromart.
(9)- Do you mind buying used scopes?
Nope, infact now thinking if I should go for a beginner level 8 inch used scope before i reach to nexstar level.
8 inch is generally not considered as a beginner scope.

But if you think you are really serious about this hobby and willing to compromise of the disadvantages of a bigger scope, there is no major problem investing in a 8-inch SCT and stick with it for a long time and thus getting a lot of value back for its price in the long run.
(10) - Have you attended a few star parties and look through different scopes?
Nope but I am planing to do so. I wasn't sure of where to go earlier but now through this forum i think it will be a lot easier.
Great! A few of our newcomers acquired C8s in the past few weeks. You should come and join us sometime and have a good look through them and talk to the owners about their experiences of using one.
