I start with the high-cost, items that have the most potential to go wrong. That way, if something blows up, I've got room to adjust the budget.
Also, I start with things that take longer - landscaping typically takes the longest to get done. Especially if I need to do a new lawn (we don't do those instant lawn carpets around here). Roof cleaning takes a while too... about a month after being washed to be fully effective. Pumping out the septic tank (gotta give time for the grass that was dug up to re-grow). Another good reason to do outside first/early is that you can take pictures and get preview listing going sooner.
One little trick I've found to work well near the end...
1) Sand and first two coats of polly on hardwood
2) Paint walls/ceiling
3) Last sanding and polly on hardwood
2, 1, 3 - The painters are happy because they can slop paint all over the floor, BUT I'm unhappy because then ALL the surfaces have to be wiped down from the dust - and it's never perfect.
1, 3, 2 - No dust to clean but Painters have to be perfectly careful and not drip OR scrape with their ladders. =Cost more and they are grumpy
1, 2, 3 is a bit more coordination, the painters sill have to be a little careful - but don't charge me extra. There is A LOT LESS dust and what there is, is not as obvious because it's clear/milky. There's a lot less cleaning labor and everything in the end looks crisp.