Pretty much everything you need can be sourced from Rare Spares: http://www.rarespares.net.au, so there shouldn't be anything that *can't* be done. A reconditioned engine is the right way to go, but buying it in Perth may make a warranty claim difficult if the car is back in Canberra when the problem occurs.
If the steering is the show-stopper then get that done first. Rare Spares had change-over steering boxes for $400+ so it doesn't look cheap but the rebuild kits were around $60 so a local specialist could still do the job. There are a couple of Australian magazines that cater to older cars and they usually have lots of ads for specialist mechanics.
Once you have a change over motor there won't be much left to go wrong given the simplicity of a 60's Holden. In my experience the big killer for older cars is blown head gaskets due to faulty cooling systems. A broken diff or a stuffed gearbox just gets unbolted and replaced for not much money. Worn out parts are just a fact of life, you would still need to replace brakes pads and discs, bushes and shocks, water pumps and fan belts etc. etc. etc. on a newer car at some point anyway.
I can't see the point in replacing the Belwood with another HK as it won't be the car that figures in your memories. In any case you would just be starting from scratch with another car full or nearly worn parts that will need replacing. Better to fix the one you have (and love).
As for buying a newer secondhand car, well I wouldn't recommend anything much older than 10 years. Anything from the 80's will be a complete lottery and I wouldn't recommend a small four cylinder if you drive on bad roads. The mid 90's are where the useful stuff like ABS became common and the bigger cars are now only worth $5000 - $6000 and if you can get one with LPG they will be cheaper to run than a mid size four cylinder car. If you want a bench seat in the front the Ford Falcon will be your only chance.
So, you might spend $4000 fixing the Belwood, or you could spend $5000 getting a secondhand car that would be nicer to drive but will be starting to wear out. The Belwood may still be the cheaper option and given the sentiment involved probably the better option.
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If the steering is the show-stopper then get that done first. Rare Spares had change-over steering boxes for $400+ so it doesn't look cheap but the rebuild kits were around $60 so a local specialist could still do the job. There are a couple of Australian magazines that cater to older cars and they usually have lots of ads for specialist mechanics.
Once you have a change over motor there won't be much left to go wrong given the simplicity of a 60's Holden. In my experience the big killer for older cars is blown head gaskets due to faulty cooling systems. A broken diff or a stuffed gearbox just gets unbolted and replaced for not much money. Worn out parts are just a fact of life, you would still need to replace brakes pads and discs, bushes and shocks, water pumps and fan belts etc. etc. etc. on a newer car at some point anyway.
I can't see the point in replacing the Belwood with another HK as it won't be the car that figures in your memories. In any case you would just be starting from scratch with another car full or nearly worn parts that will need replacing. Better to fix the one you have (and love).
As for buying a newer secondhand car, well I wouldn't recommend anything much older than 10 years. Anything from the 80's will be a complete lottery and I wouldn't recommend a small four cylinder if you drive on bad roads. The mid 90's are where the useful stuff like ABS became common and the bigger cars are now only worth $5000 - $6000 and if you can get one with LPG they will be cheaper to run than a mid size four cylinder car. If you want a bench seat in the front the Ford Falcon will be your only chance.
So, you might spend $4000 fixing the Belwood, or you could spend $5000 getting a secondhand car that would be nicer to drive but will be starting to wear out. The Belwood may still be the cheaper option and given the sentiment involved probably the better option.