Down Payment Assistance:  What do I need to qualify for downpayment assistance? 

The implication from your question screams that you absolutely need assistance and insight from an experienced, knowledgeable REAL ESTATE attorney to help you understand the risks and protections available to you in the type of transaction you describe.

What are the tasks that must be done by a property manager/owner versus someone who is assisting a PM/owner?

My wife, Magdalena, and I work together to ensure our clients have a seamless and successful investing experience.We pride ourselves on being quick and efficient in handling deals and are always available to assist.

I was in Milwaukee two months ago with my old partner visiting her mother in an Assisted Living.

I also recommend that you reach out to @Josh Green, he is the local expert in the area to assist with your home search and is also an investor himself.

FOLLOW THE K.I.S.S method plan (keep it simple and stupid).Find and hire a real estate agent that understands multiple investment strategiesGet pre-approved - see what options you havebased on your pre approved price - identify an area you want to invest in that you can affordLeverage the agent to : bring you properties, assist in pulling comparables (you should know your comparables of the area you are looking in, this is for a second opinion) review and confirm your estimated rental income, assist you with acquiring the property, and have a list of resources you could use; contractors etc.Looks at properties and make offers that work for YOU.Also,Do not pull your IRA money out, leave it there and let it grow - leverage this to meet your lenders reserve requirements.Buy Multi family to holdBuy single family to fix and flip and produce more income to buy more multi families.

@Dakota Mivshek From my recollection I think mostly I was dealing with the secretary of the company or some assistant and these people are all unlicensed, unprofessional, basically don't have any concept of how to structure contracts or even withdraw from a contract unfortunately.  

@Dar Baruchim you should see your first few investment properties and find experts to assist you.Buying sight unseen OOS is not recommended for newbies.

These strategies can serve as effective starting points for your investment endeavors.Should you wish to discuss further or require assistance, please don't hesitate to reach out.