I'm not familiar with the Union Polaris 36 but being a Bob Perry design
I'm sure it's a fine boat. I have a Westsail 32 and love it (so I'm
prejudiced

ALL boats will need some work. Not sure if $$$ is an issue but the 36'
boat will cost more to re-fit/commission. Seems the cost of
*everything* on boats increase 'exponentially' the bigger they get. It
will also cost more to maintain/operate long term. Some 'sweat equity'
in the Westsail will only increase its value which you will recoup
later.

Re-powering either boat won't be cheap. My Westsail was recently
repowered from engine (42 hp Universal M50) to prop to the tune of
about $12K. Depending on what you mean by 're-doing', the teak deck on
the Westsail won't likely be cheap either... re-caulking is one thing,
removing/replacing is another.

Does the Union boatyard have a good reputation for quality? Westsails
were clearly overbuilt (1" thick hand laid glass hull, excellent
carpentry, etc.) and have an excellent build quality.

Not saying the Union Polaris won't (I don't know) but Westsails do seem
to hold their value well. In fact, assuming it's maintained they seem
to be appreciating. Compare the price of a Westail 5, 10, 20 years ago
with that of today. How many boats can you say that about?

One nice thing about Westsails is the excellent owners group
(www.woa.org). The ex-GM of Westsail also has a company
(www.westsail.com) that supplies replacement parts & 'stuff' for
Westsails. Point being there is still good support for this classic.

Don't let the 32' length of the Westsail fool you. It's been said a
Westsail is a 40' boat in a 32' hull. It's VERY roomy below with tons
of storage. So much so there is a saying among Westsailers that
something is 'lost on board'. You know you have it but danged if you
can find it in all the lockers available. I've taken to having an
inventory/location list. One Westsailor had his boat for a year and
stumbled across a locker he didn't even know was there.

Depending on the amount of time/money you have to invest fixing the
boat up to fit your wants/needs (and paying for it down the road) it
sounds like either boat would be a good choice. Which one do you like
the best?