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Because I buy for my kids, usually, things are fairly straight forward. My 5 year knows almost immediately what lines/sets he is drawn to. The same occurs with my older kids.
With certain sets where there is the potential for a long backorder, I buy. I know that I have a reasonable return window at places. I did this with Hogwarts and Diagon Alley. I bought both almost immediately. Hogwarts was a Christmas present, so I needed to avoided the sell-out risk.
On some other items, I do wait.
Because of the backorder time these days, I often buy earlier than I normally might. On the flip, I carefully read a number of reviews. Unless we are talking about Ninjago spinners or minifigs, most items will stick around more than three months, so there really is time to read reviews. You just may need to get on a waitlist by waiting.
I bought Town Hall on the day it was released, there is zero doubt that I'll build it and double VIP points were going on, so why not?
Other sets, like Dino and Friends, I waited to pickup on sale (BOGO at TRU mostly), those were not going to sell out.
Another good example is UCS SSD - 10221, I waited to pick that up for 10% off, it will be around for years, no need to buy it on release day.
However, UCS R2-D2 I'll pickup on May 4th to get the TC-14 minifig, but the only reason there is I have enough VIP points to pay for it, otherwise I'd wait until Brick Friday to get it for 10% off.
Now that I am mostly "caught up" with Star Wars sets, I'm going to try to do the same thing there as well -- at least for the larger sets. I'll have to use a lot of willpower to do the same for the LOTR sets when they come out. I have learned, however, that you don't want to wait too long . . . .
For smaller sets, I'm learning that it can be frugal to be patient and wait for sales. Walmart, Target and so on often discount these by a few bucks, and Amazon will match, so I am learning that it is worth it to pounce when they are available at Amazon (Prime, so free 2-day shipping and no sales tax). TRU does BOGO sales and other discounts all the time as well -- they often don't work on the licensed sets, and they run out of stock on the big sets, but if you're patient and lucky you can make those work for you.
My two cents. Still new at this, and the experts can probably tell you what's really worthwhile.
That being said, you will miss very likely miss the occasional set that ends up with a shorter release window. This happened to a lot of us with the Limo/Helo, Family Home, Castle Battlepacks, etc.
It simply comes down to risk/reward. I was willing to risk missing the Family Home and did. I wasn't willing to risk missing the Limo/Helo so I paid full price and am lucky to have done so. I also almost missed Mace Windu's Starfighter but fortunately picked one up on Black Friday.
Course, some popular sets can be had at a discount earlier. Where less popular sets are the opposite. And, some popular sets end up not being available later at all. Again, the opposite for less popular sets.
Personally, if it is a set that I really want and it appears to be popular I get it early after shopping and getting it at a good price. Less popular sets? I do just the opposite. I wait to see if they will be discounted or put on clearance. And, even after EOL there is a good chance of getting them below retail.