Pumpkin Brew Day Turns into a Nightmare

This has been by far the longest, most frustrating brew day to date.

But I guess it is apropos for a Halloween beer to turn into a horror story.
I'll post the recipe and then explain what happened:

Hellish Halloween Harvest Beer
4.53 ^KG 10 ^LB Domestic 2 row pale
.43^KG1^LB Biscuit (Melanoiden) Malt
.22^KG1/2^LB Crystal Malt
2 small sugar pumpkins baked in the oven at 350 for one hour
2 orange sweet potatoes baked in the oven at 350 for one hour

I chose to mash the veggies instead of including them in the boil.
18 Grams / 1/2 Ounce Nugget Hops 60 mins
29 Grams / 1 Ounce Hersbrucker 5 mins
Wyeast 1275
(I bottled my British Mild tonight, and will rack on top of the yeast slurry)
I picked up my grains this morning and had my boys gut the sugar pumpkins and they had a great time doing it.

Everything went according to plan until it was time to chill the beer and that's where it all fell apart. The immersion chiller sprung a leak and gave the beer about 3 extra gallons of cold water. There was a lot of swearing. The only choice I thought I had was to boil to reduce back down to 5 gallons. Well, 4 hours later, I was finally able to put it in the bathtub full of cold water. I didn't dare try fixing or using the immersion chiller ( that would be just asking for more trouble).

I didn't know what to do regarding the hops or what the best method would be so I threw in 18 grams of nugget at 60 mins left in the boil and 29 grams of Hersbrucker at flameout. I wonder what the double dosing of the wort with the additional hops will lend to the beer? I tried the sweet wort and it tasted like a baby bitter but unfortunately, I didn't get any pumpkin notes. Of course, you shouldn't judge a beer on the first day so I will wait and find out.
Well, it is 4 AM and I think it's finally reached its pitchable temperature. Then, I'm off to bed. This was my first 14 hour brew day. I hope that never happens again.

Cautions for next batch.

I've noticed a couple of things that shouldn't be happening with my beer making process:

1. My efficiency is really poor.
2. It seems that I am bottling way less than 5 gallons of beer.

With my Irish red, I pulled out a gravity reading of 1.030 where it should have been 1.050. The Honey Basil was a better 1.042. I ended up throwing in a bunch of honey for the red to boost the sugar content because I don't want an ABV of 3%. I left the Honey Basil as it was and I pulled out an ABV of 4.6% for that one.
I have been struggling with hitting my target Mash temp. I'm going too low. I'm usually off about five degrees. The Cali B had a nice OG (still lower than it should be) but I hit the target temp. The other thing I don't do is stir the mash every 20 minutes. The web has paranoid me in believing that even the littlest bit of stirring will cause hot side aeration (tastes like wet cardboard). Hopefully some gentle stirring will release those sugars.
What I'm going to do different next time:
A. Stir every twenty minutes.
B. Use a 2:1 water to grain ratio.
C. Do not Mash Out.
D. Drain as slowly as possible.
E. Watch my temps carefully.

My next problem is the lack of beer. I didn't really pay close attention to the exact level of beer that reached the bottling bucket but it seems I'm missing about a gallon and a half. At least that was the problem with the Honey Basil. I added 5 ounces of dextrose to the bottling bucket thinking I was going to be bottling five gallons. Hopefully I don't get bottle bombs. That would blow.
I already marked the bottling bucket at the 5 gallon mark and will get a strip for the carboy.
A. Get a 6.5 Gallon boil going to get a 5.5 gallon batch.
B. Don't be afraid to top up with water if low.
C. Measure
D. Get a bigger funnel to pour the wort into carboy.
E. Waste less wort fluid into carboy