Put everything into spintax format, most commenters support spintax.
If you have prewritten comments already, put the comments inside one spintax and put the hashtags into groups of 5, so you'll have 10 groups (10 hashtags posted).
Spintax format:
HTML:
{comment1|comment2|comment3|comment4|comment5|comment6|comment7|comment8|comment9|comment10} {#hashtag1|#hashtag2|#hashtag3|#hashtag4|#hashtag5} {#hashtag6|#hashtag7|#hashtag8|#hashtag9|#hashtag10} {#hashtag11|#hashtag12|#hashtag13|#hashtag14|#hashtag15}
Results after spinning:
HTML:
comment9 #hashtag3 #hashtag7 #hashtag11
comment3 #hashtag4 #hashtag8 #hashtag12
comment10 #hashtag2 #hashtag10 #hashtag12
...
I worked with less comments and hashtags, but you can see that the results are already fairly random.
You can either use this spintaxed text in a tool, which supports spintax natively or you can make pre-spun captions with a tool like Spinnerchief, which can give you all the results or you can use a tool like
http://freespinner.net/.
With Notepad++ you can easily bulk format the lines of comments and hashtags into the spintax format above.
Let's say you have this:
HTML:
comment1
comment2
comment3
comment4
comment5
comment6
comment7
comment8
comment9
comment10
and you want this:
HTML:
comment1|comment2|comment3|comment4|comment5|comment6|comment7|comment8|comment9|comment10
All you need to do is:
Hit Ctrl+H, that will bring up the 'Replace' window.
Make sure that the "Regular expression" radio button is selected.
Find what: \r\n
Replace with: |
Hit "Replace All"
You just need to put the braces { } in manually. Rinse and repeat this with the hashtags and it's done.
If you don't want to spin the comments, just the hashtags, obviously that can be done too.
Just spun the hashtags with Spinnerchief, if you want 300 comments, you will need 300 x 10 random hashtags to go with the comments. The tool will produce one text file for every result, you can join the results with a tool like TxtCollector into a single file.
Then You'll need MS Excel.
Put the 300 comments into an empty file, one per line and simply paste the 300 x10 hashtags next to the comments, copy the whole thing back to Notepad++ and format it to your liking.
It worth it to learn basic regular expression commands, what you can use with Notepad++ and how to use Excel, at least the basics, so you can format big chunks of data fairly easily with a few clicks without any programming knowledge.
I remember when i started out 10 years ago, i manually formatted everything, which took long hours sometimes, with a few simple tools and commands, you can spare a lot of time.