Transom repair

[Will Gilmore]

Is water infiltration/blistering more likely at these spots,

Of course it is. I would say that damage looks like storm damage at a dock. You said in the original post that the damage was a couple of storms and a collision with another boat. You could be looking at cosmetic damage or you could be looking at broken fibres from being slammed hard. What does the inside of the impact area look like?
Personally, I hate fiberglass work because it can get seriously itchy if the job is big. However, fiberglass is easy to work with. I just think there are known and unknown problems that will need to be addressed and they aren't small ones.
Looking at the listing, I can see why you are interested. She is nice below and the motor looks ok. The bowsprit looks like neglect, in my opinion and that leads me to suspect other undiscovered issues unrelated to the damage.
Here are some alternatives. They might be in better or worse shape but, if you're shopping, take a look:
https://dallas.craigslist.org/mdf/boa/d/columbia-30-sailboat/6401749025.html

https://dallas.craigslist.org/dal/boa/d/sailboat-32-ft-ketch/6409667965.html

https://dallas.craigslist.org/dal/boa/d/1982-hunter-27-sailboat-boat/6393265492.html

http://m.sailboatlistings.com/view/68249

http://m.sailboatlistings.com/photographs/65838

- Will (Dragonfly)

 

[pateco]

Here are some alternatives. They might be in better or worse shape but, if you're shopping, take a look:
http://m.sailboatlistings.com/view/68249
- Will (Dragonfly)

Of those you listed, this is the one that would interest me.

 

[Ward H]

It sounds like you already decided to walk but I will add my 2 cents.
Most of the post were talked about the fiberglass damage. One thing I would be worried about is the standing rigging. With the chain plate of the split stay being in the area of the hit and also being bent, could the stress of the hit traveled up the aft stay and stressed rigging components? Another unknown that could add cost down road.

 

[Will Gilmore]

Of those you listed, this is the one that would interest me.

I found the hobie very interesting too. The accommodations look sparse but easy to work with. I didn't think the Oklahoma address was too far away from you.
That are a lot on the Dallas area, Huston and Galveston would also have a lot.
Ward H is right. No one even considered what damage like that could do too rigging.
Good luck.
- Will (Dragonfly)

 

[kbgunn]

It sounds like you already decided to walk but I will add my 2 cents.
Most of the post were talked about the fiberglass damage. One thing I would be worried about is the standing rigging. With the chain plate of the split stay being in the area of the hit and also being bent, could the stress of the hit traveled up the aft stay and stressed rigging components? Another unknown that could add cost down road.

You are right and I had not even considered this aspect of the damage. The impact could have popped the chainplate instantly or applied a downward force on the masthead until failure. The downward force on the backstay would translate to an upward force on the on the bowsprit and foreward lower shrouds! Another good reason to pass....
Thanks for the $0.02!