Usually when you're that far off you are wasting time as the seller is unreasonable, I'm actually a bit surprised you actually got a counteroffer and response at all. 

If seller is serious, they would put in a counter-offer and our negotiations would start there.

I was about to respond to a counter offer i had made when all this went a little nuts.

Personally I like the offer, i dont want to lose this offer, I might counter offer with $545,000.

The seller's agent says that they don't like the closing date and insist on moving it 15 days ahead (side note, I am offering them the same terms as one of their previous counter offers, and there isn't even anyone living in the house right now.

Are you getting any feedback from Sellers at all (i.e. counter offers) and if so what about your offers aren't appealing to them? 

A large depposit certainly makes you stand out enough to make you a counter offer.

I am holding my counter offer for the property as follow.Location: IL Northwest Suburb (Barrington High 220 district)Type: Single Family House (2car garage attached / 2 bed / 1.5 bath / fully remodeled (rehab in 2019)Listing Price: $320,000 (Holding counter offer of $310,000) / 20% Cash Down with Conventional LoanLot Size: 10,000 sqftPrimary Residential Purpose, but market price for rental ($1,900-$1,950 / mo)Issues/concerns:1.

The only issue here is that it seems like my offers are coming in quite a bit lower as I am not really getting much interest in counter offers. 

Counter offer: $235K, 7 day inspection period.