Not a silly question at all but the answer depends on a few factors.

@William Causey depends on the transaction and the parties involved.Agree with @Dennis McNeely on some of the transaction costs.A different issue though is with an Assignment, the buyer gets to see what you paid for the property.

Lending options will look different depending on your answer.

. # of times you talk with your CPA/tax planning (generally tax planning is going to cost more)It depends on the CPA, location, etc.

Depends on who you are working with and how much time you put into it.

So its really all depends right.

Depends on the exact soil.

Deduct NEW property taxes after you buyDeduct home insurance costsDeduct maintenance percentage, typically 10%Deduct vacancy+tenant nonperformance percentage(we recommend 5% for Class A, 10% Class B, 20% Class C, good luck with Class D)Deduct whatever dollar/percentage of cashflow you wantNow, what you have left over is the amount for debt service.Enter it into a mortgage calculator, with current interest rate for an investment property, to determine your maximum mortgage amount.Divide the mortgage amount by either 75% or 80%, depending on the required down payment percentage - this is your tentative price to offer.If the property needs repairs, you'll want to deduct 110%-120% of the estimated repairs from this amount.Be sure to also research the ARV and make sure it's 10-20% higher than your tentative purchase price.As long as the ARV checks out, this is the purchase price to offer.It is probably significantly below the asking price.

Whether you consider that good or bad depends on whether you are a buyer or seller. 

The answer to your question depends on the opportunity you have with your property.