Love planning - I actually quite enjoy looking for our accoms - I tend to airbnb now, and I'll spend a few hours looking for accoms in each place, and I'll make a wish list, then pare down the wish list, make notes, get a top 10, narrow to top 5, then top 3...(then get disappointed that I took so long and my #1 choice got booked...lol).
I usually know a year (or two - 2019 - Venice for Carnival!) out where we want to go (next year - Scotland in May!). About 8 mos before I'll do some light planning - decide maybe where to go, what to see, how many nights...then I'll totally ignore it for a few months, then 4-5 mos out I start my airbnb/accom search, pin down our flights, then do the booking...then I ignore it again until about a month ahead, when I really start getting into planning how to get around via public transport (or car if we are renting, which is rare), checking opening days and hours for places, writing down day trips from anchor locations, having my must sees and 'if we see it cool, if not, cool' sites...in a former life I would have been a travel agent...
It does take time tho, and a lot of people def have a time deficit these days. It's easy to get frustrated and settle for accoms, so I'm glad I can have the time (and patience) to sift thru dozens of listings and reviews. But I get enjoyment out of it (I'm a planner!)...def not for everyone! My sister tells me she's going to have me plan her trips for her...
And I love seeing the end result - on the plus side, I get the praise from hubby when I find something neat and unexpected to see (thinking of when we went to LA and I took him to the Bradbury Building, which featured in one of his fav movies, Blade Runner, and he was just tickled that I found out about it)...then again, when my planning kinda fails or is lax, then I get the blame (thinking of when we just tried to go to Kinderdijk, didn't check the online map to see exactly where the bus stop was (too early in season for direct ferry) and we ended up missing the bus stop and wandering around for a bloody hour before finally finding a bus stop to get us there.)