This could actually work. There were a lot of worthy ask blogs that weren’t included back in Ponibooru, so this could tackle the daunting task of uploading each entry!

If somepony wants to tackle the Trixie Asks they can have it.  
There seems to be:  
ask trixie (lesbian Trixie co starring fluttershy, sometimes tagged “ask trixie and fluttershy” on PB)  
ask the great and powerful trixie -> 2 of these and the 2nd does not have a consistent artist?

2 Please

option 3: but please don’t dump 20 images in one go, spread those from each blog out over a few days

+thanks for @bustoblaster for Ask Velvet and Smartie Belle. :D

^yah, true  
also *chubbies

#3.  
Especially The Daily Derp.

^about ask japplejack, you facts are wrong, no a single pic of the arc after apple bloom dead had been posted here.

some more  
ask meanie belle: 10 pics  
question pinkamena: I uploaded a few from this, not sure if I will do more
 
Also, “madmax silly comic shop” is usually treated differently than the above ask about ponified madmax and her friends Bitchdancer & Midnight Fun.

I tried to make a list of the tumblrs that have more than 1-2 images. I hope it helps a little.
 
Currently “ask” gives 650 hits, “tumblr” gives 500.
 
ask Molestia (John Joseco): appr. 20% uploaded  
ask Futashy  
ask Jappleack: 100%  
ask-four-inept-guardponies: (mostly) uploaded by the author  
werelight shine/twilight unbound: uploaded by author  
ask princess luna: some =the better ones) uploaded
 
ask: 650, tumblr 500  
ask pipsqueak the pirate: mostly uploaded (pretty short so I may complete this soon)  
bipolarity (ask bipolar Rarity): 90% done (may need some source fixing)  
flutterdashpie by cartoonlion: mostly up? (doubles as art blog so difficult to tell)  
ask loony luna: I think the artist uploads it here regularly  
ask spike da dragon: a few uploads  
ask pinkamena diane pie, AKA ask blinkie pie: (the “good” pinkamena blog, where Pinkie remains a cheerful rock farmer) lot of uploads and properly tagged, may need some unuploaded pics to be filled?  
ask gamer ponies: consistent uploads. seems in order. (not sure if it misses anything)  
ask the pie sisters: only a few uploads, needs moar  
asks the cmc: a few strips  
ask a mailmare: a few uploads but missing tags  
ask blueblood: needs “artist:ttturboman” tagged more often. Otherwise good. Only part uploaded yet.  
ask iron will: some uploads  
ask mayor mare: many uploads, well tagged  
ask cloud kicker  
ask lady octavia: this ask is DEAD. 4 images known, please fill if you have others.  
ask gabby gums: fully uploaded (very short blog, dead?)  
ask roxy in ponyville: crossover blog.  
ask applejack  
ask my little chibbies  
ask discopie  
ask princess fillies
 
 
Things to look out for:  

3

3, I suppose. I don’t mind seeing old tumblr posts, and Poni/Derpibooru is how I’ve found a number of ask blogs that I visit regularly.

3

Three.

btw I’m not implying that me or anyone is trying to do all the work. :p  
This was just to test the waters if these mass uploads will be welcomed.  
If you want them up, you have to do it mostly yourself. :p

So pretty much every one said they wanted the old tumblr stuff, so you may be seeing a lot of classic asks uploaded in the near future.
 
Derpibooru has very few Asks up yet, so it’s a free-for-all. If you know of tumblrs that went offline since, it may be a good idea to loot Ponibooru for them.

I can’t see the votes, for the threes.

3

3

As such, I support option 3.

I’ll say this: all of the pony tumblrs, and some non-pony tumblrs, that I follow started from me seeing a dated strip on here or Ponibooru.

3 kinda? I don’t think every post on every ask Tumblr should go here.

Number 3 is the best; I would never have known all those marvelous ask blogs if it wasn´t for the kindness that uploaded them periodically in ponibooru.

for 3

I vote in favor of option 3.