I see the value if I'm facing a massive tax bill, receive a 50%+ DP, or I could see the value if I'm offering seller financing to a qualified buyer will owner occupy. 

It's a great idea to get this up front before paying them so they have an incentive to give you the information. 

I understand that as one acquires more types of assets, taxes can become more complex, and I want to ensure I'm maximizing my savings.Are there any CPAs in this community who also own real estate and could offer guidance or share their experiences in navigating taxes as a real estate investor?

We actually coached a client to offer a dog photo shoot at his hotel because so few in his area allow dogs.

I like to figure my estimated cost before I make an offer on the property.

I was prepared to offer $15,000-$$20,000 to buy it outright. 

I think it would be fair to ask for 1/3 of that savings as an incentive to assume the loan... so approx.: $36,000Fair?

In order to make sure you're optimizing your tax advantages and adhering to all applicable requirements, even while I can offer broad advise, I suggest speaking with a tax professional or accountant who is knowledgeable with real estate taxation.

The market is slightly less competitive and offers 5-10% more value, the last Triplex we sold in the area was for $500K and a recent duplex in Salem at $420K. 

Even if you offered her tons of money.