Here's my experience with outdoor growing

I've been growing in my basement for a few years now and am pretty good at it with good yields and no real problems.
I don't know how the guys in humboldt county get by without problems but I've seen nothing but pest problems as soon as my girls were old enough to have problems.
I have 3 plants and they're spaced about 6' from each other to allow decent airflow between them.

The first problem I had with was powdery mildew:
This started right around the beginning of flowering (early-mid August) I plucked quite a bit of the impacted foliage off, hand washed some of them foliage, and finally treated with neem oil with so-so results. I couldn't get in front of the pm problem as it always returned.

2nd was bud rot:
I had one girl that had amazingly tight buds (grapefruit diesel from pheno finder). This was expected to be over 1 lb of weed. I noticed that some leaves were dying off and upon closer inspection, a lot of nugs with bud rot... WTF . I ended up knocking this one down about 2 weeks early to make sure that I could get something out of it (maybe 5-6 oz).

Finally bugs:
I'm guessing moths are dropping eggs off and thereby turned into wormy or caterpiller like things. This pisses me off because they shit in the buds and I've been clipping them off and throwing the buds in a kill bucket (bleach water). I've read ladybugs can help with this so I'm going to cover the plants up with mosquito netting and releasing them under the net.

My conclusion:
Unless you can control the environment with a positive pressure greenhouse, I would stick growing indoors during winter months. Growing weed is supposed to be a happy activity. It's not worth the aggravation of watching your hard work go up in mildew and bugs.

Nothing is foolproof, but outdoors an ounce of prevention is worth a pound of cure. It sounds to me you were late to the game with any treatments. These should be at least weekly from he time they go out to harvest. Btw if the plant had lots of buds with rot you shouldn’t use any of it imo

Bugs start immediately not sure how it was your final problem as they usually are there from a he time you harden your plants. Indoors and outdoors are 2 completely different methods that require different attention.

I'm in a slightly better mood now (and exhale).
The bud rot seems to stay very local on the plant and everything above and below the affected areas seemed fine. I imagine that if I let it go it would have taken down the entire plant. I followed the guidelines of growweedeasy and took the advice of harvesting early because of this problem. I didn't notice any bugs until the flowers were well on thier way and the leaves were getting sticky.
I'll try outdoor growing again next year but not without building a greenhouse first and a continuous supply of ladybugs.

2 most important things for indoor growing
#1. fresh air exchange
#2. sanitized / clean grow space

PM / Mold / bud rot is caused by not enough air circulation and not enough fresh air exchange
This in turn makes your plants unhealthy, which attracts bugs
all it takes is you coming in from say an outdoor walk and some bug hijacked a ride on your clothes and they will seek out the smell of sick plants looking to infest. If your plants are healthy the harmful bugs usually are not interested.