- for you = it's better to pay for the repairs, because you won't be living in the place anymore so you don't need to hire "the best" contractor.
- as a buyer = I would never purchase a house where the seller did the repairs for this reason.
The buyer cannot use an FHA or other government subsidized loan, unless the place is move in ready. Peeling paint is not even allowed.
Based on how you describe the house, you would not be eligible for a FHA lender, unless you did significant repairs. A conventional loan lender better much wants to make sure the house will be standing in a few years.
Note: you have to disclose all known issues. It doesn't sound like you knew this.
You can call it a fixer upper and sell it for less than market price, there is a disclosure report where you have to give up as much information as you know, and there are a lot of questions.
The problem is that they will still want further discounts --- even though you reduced the price. You are better off fixing the things that need fixed.
Are you selling by owner or using an agent....usually when you say "as is" you price it to sell based on that. The thing is no matter what the price is people will still offer less. If you use an agent they can tell you what things have been selling for and things in your area that are similar to yours by size and condition. Are the repairs just to pricey ?
talk to your realtor about this. they deal with this kind of situation all the time.
I figure the buyer's inspection will find a bunch of stuff that needs work, and that the buyer will want to take that off the price of the house. Is it possible for me to take it off in the advertised price, to get more offers sooner? But not have to deal with buyers trying to double dip, taking the discount a 2nd time, after their inspection? If I simply sell it "as is" for the discounted price, will that cause a problem with the seller's mortgage company?