Just remember... You have the power right now, and you have the ability to move up in price from where you start so just ask away. Just be willing to say yes at some point.
2. If you are working with an agent you shouldnt be looking at houses you cant afford.
3. I agree with wholy and this should be the main determing factor. what are you willing to pay for the house? Before submitting an offer the agent should go over with you and ask if this is the highest amount you would be willing to spend and risk losing the house. If its not then either take the chance that someone puts in a stronger offer or you make a stronger offer yourself. You cant count on anything.
Select the lowest number from the following three: (1) comps, from a CMA, (2) what you're preapproved for, and (3) what you're comfortable spending. Then look at the listing price. If it's higher, stick with the lowest of those three numbers. If it's lower, drop your maximum down to the list price. That process gives you the maximum you can spend on the property. Offer aomewhat less. How much less depends on how aggressive you want to be, and how much you want the property.
Get comps to make sure you're not OVERpaying.
Simple rule of thumb about pricing.. What is it worth to you?
Sounds too simple to be true but ask yourself before you write the offer what is the absolute most you would pay and if that is the highest you go and you are ok with the risk of losing the property to a higher offer then you won't be sorry for your decision.
As far as pricing.. the house is already discounted. There will be competition regardless of how long it is on the market. Never count on days on market to figure out the price because it has nothing to do with how the price is determined.
There is never a blanket strategy in making offers on any property. You have to know the property, the market and deal with them one by one.
Go for it. I respectfully disagree with Lee's answer about tax assessment particularly in Wisconsin where assessment can be 100% of the home's market value depending on your municipality. Have a figure in mind of what you're willing to pay for this property based on repairs, neighborhood value, and your budget. Hopefully you are working with a good realtor who can help you determine these factors and good luck with your purchase!