Offer on a multifamily well below asking price

[Kyle Garro]

I am interested in putting an offer in on a property. The current rents can support 2800 gross per month for all 4 units. C class unit with some deferred maintenance that will have to be addressed on a ten year time line. Asking price is 335k which is high by about 35k at least in my opinion. My question becomes, do you place an offer that is much lower than the asking price and just see what happens? Or do you talk to the agent first to see if it is even worth it? I don't want to make any enemies as this is a small market but the prices i am seeing are just way over the 1% rule and honestly don't make any sense as i run the expenses on some of these properties. As a general strategy, is it poor form to throw in a low ball offer or place an offer with the intention of finding something wrong that will allow you to retrade the deal (i know this is questionable)? Really tired of just passing up deals because the numbers just don't make sense and want to start getting in the game. Thanks in advance for the help, all.