Hi guys, I'll be up front and say this isn't a job I can/will do myself.
@jhrobbin , you get to be the ultimate arbiter of whether you will paint your house.
But I'm going to question whether it's true you can paint your house.
A huge % of houses are very simple to paint with very inexpensive tools. If the weather is nice outside and you don't have to finish super fast, it's actually quite pleasant and meditative. I know this because I just painted the outside of one of our rental properties. It was a nice enough job that I would consider doing it as a side hustle just for fun.
And yes, I'll assure you that I paid attention to where the sun was when determining where I would be painting next. It made a big difference in comfort.
This is not a job that requires any special skills or intensive training to do a good job. To do a perfect job? Sure, that's an order of magnitude harder. Few of us need a perfectly painted house when the savings can be in the $4000 to $8000 range.
$4000 to $8000 in savings?? Is this a typo? How big of a house are you painting?
Not a typo. I painted 85% of the exterior of my house last spring. It's a 2 story, 3000 sq ft craftsman style (aka big gables above the 2nd floor, setback 2nd floor and a shit ton of trim) and we only called one company for a quote. Their bid was $6800. From talking to other homeowners in my area, I think that quote was actually too low and comps would've been in the $8-10K range.
I went all out and bought the 2nd highest grade of Sherwin Williams paint, rented a huge lift (to reach the awkward 2nd floor and gables), and paid someone to pressure wash the outside to prep it. It still only cost me $1500. This summer I'll rent some specialized scaffolding to reach the last section where the lift wouldn't fit, but I'm sure it'll be less than $600, including having the rental company set up and tear down the scaffolding.
In terms of time of year, check the temperature guidelines on the paint you buy. Different brands and grades have different high and low temps. The type of siding you're painting may also matter. I've got hardiplank siding with cedar trim. The hardiplank is basically pure concrete and gets really hot. Even early in the morning the paint was steaming as I applied it. Didn't make any difference though. It dried nice and still looks great. The wood trim doesn't get as hot, so application was less exciting.
I'd skip painting in conditions that are hotter or colder than the application temp for the paint. I'd also skip painting on seriously wet days (SW makes a paint that can go on in somewhat wet conditions though) or very windy days. You don't want to be on a ladder in a strong wind and you don't want dust or other debris sticking to the wet paint.