My current entity structure is that I have a WY LLC as my Mother company and a MI LLC as my real estate holding holding company in MI.

Landlording is a business; you didn't get into this to be Mother Teresa.I understand this may be easier said than done; therefore in your case it's probably in your best interest to hire a property management company if you find yourself unable to separate your personal feelings from the business.

Elderly mother can help with $ but is not rich herself and obvi taking retirement $ from one's parents is a worst-case scenario.

Prospective client is renting as a guarantor for mother in law to live nearby him, proposing to do a 2 year lease, mother in law who will be the occupy is retired so all credit check and income is based off daughter and son in law.  

I can definitely answer your question, here's what I did with real examples.1st House Hack - 4 unit - I purchased this multifamily in August 2017 with 7% down (couldn't do 3.5% down because of the FHA self-sufficiency test).   2nd House Hack - 1 unit (single family house with mother-in-law apartment) - I purchased this property in the summer of 2018 with a 5% conventional loan (a little over a year later), and I was able to move out of my unit in the 1st House Hack and into the basement apartment of this house hack.

Last week, I received a call from my mother that she wants me to take over her house since she's retiring soon.

Three months after they moved out on their own for a bigger place ( thank God), me never receiving a call for a reference, some lady comes to my door asking me if her mother called me about them.

I can probably track down an address for a pocket of small MF in Norcross if you're interested.The good news continues if you're ok with going the SFH w/mother-in-law suite route.

(My mother pushed, so I was lucky to go to the best public high school in the area, since I said grew up in the city 😉). 

I'm in the navy and I'm off from sep 1- oct 20 then I have less than a year before I get out so I'm free pretty much anytime other than the 9-16 as I'm going to Florida to visit my mother.