Since you are buying for yourself you are not acting as an agent but there is the potential that if you don't disclose that you are an agent, a seller might say that you took advantage of them by being 'more knowledgeable' and buying at a discount rate.That being said, I plan on still getting my license so that 1) I have access to the MLS 2) It can greatly expand my network and 3) it opens the potential for referral fees for houses that the seller insists on retail price.

My plan is to either hold the properties for long term rentals or possibly "wholetail" them depending on what kind of financing I can pull together.My biggest question would be what type of discount can I reasonably expect to get for buying all four properties instead of the seller having to sell them individually?

It is a very deep discount.

Wholesale lenders or standard lenders with a wholesale department typically give discounted rates through Mortgage Brokers since we are bringing the client and handling the loan processing for them. 

What sort of discount are you getting from your neighbor since he's saving realtor commissions?

Of course, within notes there are easier and more difficult approaches such as buying up performing notes from an investment provider (turn-key) to shopping for discounted, non-performing notes.In a perfect world, one would create a portfolio that has a nice balance of different properties and notes of various types in different markets to achieve diversity - as well as perhaps some traditional equities/funds, maybe some precious metals as a hedge, etc.A budget of $100K could most likely be placed into one or two key investments.  

We will only do this if we can get at least a 20% discount on the property so we can have decent equity in the property.

Depending on how bad the repairs are, you may also end up giving additional discounts, especially if the home is only going to appeal to a professional investor.If you're licensed and still not sure how to arrive at a valuation, it may be in your best interest to hire another realtor to sell the house for you.

Are there better ways and larger discounts?

What with the military draw down reducing housing demand in the area, I might be able to jump in on this for a heavy discount, especially if the seller is highly motivated.