Sending money through Western Union (5 Dimes)

Hello all. I know that this might sound like old and repetitive to some, but this would be the first time that I would deposit via Western Union. My question is, if I want to deposit a fairly large amount, say around $2000 through Western Union, would it be safe to deposit it all at once, since it would be my first time depositing through this method? Or would I get flagged or something by Western Union? I've heard a lot of different stories: 

i would deposit it in 1 lump sum,the more transactions you make the more red flags,i have been banned from wu and mg for 8 years

There's probably a lot of different opinions on this but for some reason anything over $1000 seems to throw up flags at Western Union. I use them occasionally and keep the transactions fairly small and it's no problem. There's better deposit methods out there with a lot less potential hassle.

Stay as far away as you can from Moneygram. Late last year, they got some new head pencil pusher in their compliance department that has a hard on for gambling. Unless you're sending $25 to someone or paying a bill, they'll flag the transaction if it's going to the usual countries or the usual names. You know what I'm talking about. It's a hassle to get it back so Moneygram isn't a good option. 

Slice...I'd say send it in one lump sum, or if you are worried, send 1k, wait a week or so and then send the other 1k...ive used both WU and MG, and rarely have an issue, be sure when you do it, you double check the spelling of the names when the clerk fills it out on the computer from the form you give them...a few times i've left the store to call in my deposit only to see they misspelled the name, which just makes you have to call wu or MG to get it changed...if you have any questions let me know, what book you trying to link up with?

advice i was given once for depositing was not to deposit a round amount.  Instead of depositing $1000 thru MG, use $978, or $1019.

Damn, I used moneygram for a withdrawal the other day and it went through good. Don't want to do it again, if this is true...

It must be hit or miss for everyone because I have sent and received more MG transactions from all the usual countries and names than I can even count and have never had an issue at all.