Per subject.
At this moment, 282 hookups to 1 HCDR and SN1 as power amp.
Your honest options and advise. TIA!
Sell the SN1 and get a 250DR.
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Supercap non DR into Nac 282.
+1
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I’d agree that a 250 DR is going to bring a better result than adding another HiCap. Obviously, the 250 DR is a more expensive option, but selling the SN1 combined with falling 2nd hand prices for the 250 DR may make it easier.
There is no shortage of threads on here, about the use of 1 HiCap, 2 Hicaps or a Supercap with a 282 or 82.
Search is your friend here… 
PS. Yes, to the 250. A 250 makes anything better…
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This is another vote for a 250 of some sort.
For powering the 282, imho SC beats 2HC beats 1HC, but the change to a 250 is a good deal bigger than either of those. Personally, I would only view going beyond 1HC as good value if it is part of bigger changes - like getting a Supercap because you know that sooner or later you will step up to 252 (or 52) from your 282.
Do you have a firm idea what your SN1 is worth second-hand?
A 250DR may well not be cheap. However, you can probably get an olive 250, serviced in the last decade, for less than £1K on eBay or PFM.
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What’s your source? I’d start there if needed then 250 before 2nd hicap
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The NAC 282 was designed to optionally receive two voltage (24V) rails per channel, of particular significance is feeding each channel’s gain stage with it’s own dedicated voltage rail straight from the PSU. If Naim engineers didn’t think it made a difference why even bother with modifying the preamp’s architecture, this facility is no small feature. Unfortunately I don’t have the answer to how much of a difference it will make over a single HiCap, too dependent on many other factors IME, you may need to borrow one or buy with a return guarantee to be certain. What I can assure you is that upgrading your power amplifier is largely irrelevant to your question, it’s sad to see how many threads derail into the tired naim upgrade frenziedness.
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The OP asked for honest options, presumably meaning opinions, and advice. My advice is to get a 250 rather than a second Hicap. That’s not sad, that’s honest advice to help the OP spend their money wisely.
I’ve used two Hicaps, albeit on an 82, and know that the improvement from a 250 is way bigger than adding another Hicap, which some consider a waste of money.
If the sale of the SN1 is added to the money for the second Hicap, it won’t cost much, if any, more to get a 250DR, and the system will be a whole lot better. And that’s got to be a good thing, surely. It’s nothing whatsoever to do with upgrade frenziedness, if frenziedness is even actually a thing.
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I agree it’s much more important to upgrade the power supply on the Nac 282 as it’s earlier in the chain.
A Supercap makes it an absolutely fantastic preamp.
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I had 2 HiCaps for a while and I would stay with one or get a Supercap. I used a Supernait 2 as my power amp until my 250 arrived. If your speakers are inefficient you should look at 250 or 300.
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The price for a used HCDR is about SGD1.6k and Supercap(Non-Dr) at SGD3.2k. Dollar wise make more sense to go with HCDR. Sound wise I know the Supercap would do a better job. Hence, just wanted to know the experience of the members here running 2HCDR into A 282.
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A 300 would be a bigger improvement over a 250, but It’s still irrelevant to the OP question, and so is financial advise, the OP didn’t ask for either.
It’s very important to have the two HC’s of the same age and service history as it’s one HC per channel.
The improvement in
musical flow,separation,broader soundstage is big.
That said I would sell the HC DR and go for a Supercap non Dr as it’s even better take it to a level where you don’t have to think about pream upgrade until Nac 552.
Amen
If you sold your current HiCap and then bought the Supercap, the actual cash outlay is minimal. That’s one reason using dual HiCaps makes almost no sense. The cost of 2 HiCaps vs. 1 Supercap makes the decision quite easy.
I’m in agreement with a few of the others. Buying a 250 will improve your system much more than adding another HiCap.
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I was told that if you put 2 hicaps, they should be matched, as each one will power a single channel, if they are not matched the 2 channels will sound different.
Matched means they should have a serial number that is pretty close one to the other.
sell hicap and buy supercap is one way to avoid mismatch and should sound better
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Declaration of Bias - I own an 82 with 2 HiCaps - and a 250.
When I got my 82 I had just my one, existing HiCap - and my long serving 250. I added a 2nd HiCap because I could get one for GP£375, pre-loved. It was/is a close match to my existing HC - a bit newer, but with the same H&F transformer. Both HC’s have been serviced.
The OP has a a SN as their power amp. So… IMO… it makes more sense to add a NAP and loose the SN. A 250 would be nice, but a 200 or 180 would also work well, I would wager.
Only after that, would I then think about further PS options.
Just my view… YMMV… 
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Yes, to matching - but perhaps not to this degree…? I think the same years give or take a few would be enough. Mine are 1986 and 1990. The change from H&F to Nuvotem was at the end of 1992 - so 1993 onwards have Nuvotem transformers.
(I will ignore the possibility of a St Ives transformer here, as I have no info.
@Richard.Dane will likely know.)
And - obviously - do not mix DR and non-DR.
A Supercap does mitigate this - but at a higher price.
And… its the ‘Gateway Drug’ to the 252 or 52… 