1: What figures do you really want but you think have just gotten too expensive compared to their original price to warrant buying?
G1 Dai Atlas, Victory Leo, G1 Trainbots, Road Ceasar, Galaxy Shuttle, Actionmaster Elites Turbomaster and Windmill
2: What figures have been too expensive but after years of patience you finally found for a reasonable price?
G1 Bumblejumper, included in a BIN group lot with him in it, he turns out to be around $30 if I split the final price I paid for the lot.
G1 Frenzy (Takara version) - found it in a Bookstore in Phils costing around 100 pesos ( again divide by 40 to get dollar conversion) which I thought oh wow, they don't know what they're selling!
G1 Abominus loose - paid Php2,500 or it, it had all the combiner parts but not the individual guns, I thought the price was alright so bought it staright away for that price, heck I pad for almost half that for a minibot, and here I see 5 robots and a combiner (plus combiner parts) for that price... it was a steal heheheh
Fort Max - Thank goodness for Encore.
Trypticon - Gutsman sold it to me for less than $200, ballpark, can't recall exactly but I know it's less than $200
3: What figures did you know were way too expensive but you ended up buying anyway?
waaaay back when I was younger and just grabbed on to any G1 TFs I could find - this was before the Takara Book type release was even a rumour.... I paid for G1 Powerglide for 1000 pesos ( divided by 40 for conversion to Au$). I was thinking it was way expensive then but I did pay for it anyways coz I don't know if it's ever gonna be reissued... grrrr, it did. 
ah well. it's still with me.
G1 Overlord - coz he aint gettin a reissue any time soon... and I needed him to finally complete my G1 collection (US released characters only). Plus he was offered to me cheaper than ebay priced (still it's gone way up price wise thru the years so I considered it ... acceptable) and I did get to pay for it in terms and staggered heheheh...
Wanted AM partner Vanguard, Myclones Dirge, G1 Victory Leo, e-hobby Dark scream ( the black version), e-hobby Magnificus
Parts- AM partner Basher-side guns, G1 Actionmaster Elite Windmill's blades[I][B]