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Krisflyer does not & will not status match, I’m ‘paid’ gold with Thai and Qantas and had 3 paid return business fares with Singapore booked in the pipeline that was going to put me into gold as well but they still would not status match me.
Although if you have status with hotel chain Shangri-La Golden Cirle you can be status matched after 3 legs with SQ after linking your accounts (another article on this site) The Ultimate Guide to Shangri-La Circle - Point Hacks
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That is a really healthy points balance right there. I’m jealous 
2 a & b) Where are you flying from? East or West coast?
When users like myself have some times have a bit of time to kill we can search it for you and help you out a lot easier.
Krisflyer is generally no cheaper in return (for awards), than it is one way, i.e if its 50k miles one way it will be 100k return, they don’t discount return like Cathay and a few other airlines do. But if you break the trips down into one ways it all depends on what zoning some fights are in, This is how one ways can become more costly.
So if you were to book ‘XYZ’-SIN-MNL-SIN-LHR-SIN-‘XYZ’ all in separate one way bookings which not only is messy and painfully time consuming. It does also end up being more costly in miles. Because it costs the same to fly to Manila/Bangkok for example as is does to just Singapore. For example I always go PER-SIN-BKK, It cost the same for PER-SIN-BKK as it does to if I was to only Book PER-SIN because Bangkok falls into the same zoning as Singapore… along with Manila also!!!
So breaking the booking down in one way trips in your example is not the best way to book or saving of miles.
so ill show you the better, easier and cheaper examples.
I’ll use Sydney as an example for your home base for real figures
You could book SYD-MNL (116k miles return) + SIN-LHR(170k miles return) in 2 return bookings and use the free stopover opportunity Krisflyer offer… Use this stopover in Singapore which enables you to use your other booking to fly to London & back, In total will cost you a total of 286k miles
This keeps the separate bookings down to a minimum and saves miles in Aus to Asia zoning on the SYD-MNL legs
Yet another option is you could book SYD-SIN in return, Then SIN-MNL in a return booking & the SIN-LHR in a return booking.
But this way ends up being more costly in miles similar to like I mentioned before
116k-40k-170k respectively, so blows out to 316k miles
I had struggled to search from SYD-LHR on Singapore’s site but did eventually get past the issues to find a return trip in business from SYD-LHR for 210k miles on the saver award. Then add trip from Singapore to Manila return is 40k miles. You will have to utilize a free stopover to achieve this. It works out 250k miles total business class whole way which is the best value example.
Before changes to Krisflyer rewards only last month we used to get a saving of 15% off of miles used to book online, and also it was slightly cheaper in mile cost.
But recent changes cancelled the discount as well as made it more costly in miles.
So the incentive to book online has gone out the window, You can simply CALL them, I rate their customer service and booking skills pretty good over the phone. Could take a lot of pain out of trying to book it yourself just be careful you will have to instruct them on what you want so you are only coughing up say 250k miles vs the 316k miles Our take on KrisFlyer award pricing changes March 2017 - Point Hacks
2 c) I have to be honest and say booking fully-flex or premium economy and then upgrading to business is probably not the best use of your hard earned cash and Krisflyer miles to fly with Singapore Airlines. Unless you got reimbursed from work or whatever that then would be fine.
Seeing upgrade-able fares have to be either premium economy or flex economy to upgrade. It is costly cash wise and is still costly in miles value as well.
I believe outright Business class redemption is the best value and I’m sure many others will agree.
Booking award flights 2-4 weeks out is challenging and risky in most cases you will not find the seats,
Book award seats earliest as possible, It will often be the difference whether a seat is or isn’t available.
There is also the hurdle/feature with Singapore where they can wait-list your saver award seat if one isn’t yet directly available to redeem. You will have to read up on that I cannot find a guide on this site. Basically you have to wait to they approve your request for the award and then they give a window to book it in.
Anyway hope this all has helped. Happy remdeptions
Kyall