Are the units vintage quality with in-place rents $500/mo below current market?  

Each unit is $725.

We are thinking about furnishing one of the Racine duplexes and listing it as a MTR to maximize our investment and get a higher cash flow. 

It is a 3 unit airbnb portfolio with each unit in a different city.

Can anyone give me some advice pros/cons on having a single family unit with a pool as a rental unit.

To get those hours, maybe turn one or two into medium term rentals (you want the average stays to be over 7 days so they don't fall into STR status) which would give her more to do, particularly in the first year of furnishing them and getting everything set up.Alternatively, she maybe she could manage the properties but also get her RE license and try to sell a house or two a year - go to lots of open houses or run them for other agents?

I can do this as I manage over 60 units and it makes the most sense, and I beat the market every month.If I had 1-5 units, I would like use PriceLabs (or Beyond Pricing) and use their base tech as well as manually checking things at minimum weekly.

Remember, I sent a signed and amended the agreement on November 28th, sent it to them for signature, received confirmation of their receipt, wired funds, requested multiple times they send me the fully executed agreement, never received a fully executed copy back from them and finally was questioned by them yesterday as to why I altered the agreement (meaning there was no meeting of the minds since it's therefore proven that they didn't even look at it).I have rescinded my offer to enter into a contract with Estate Legal for lead generation services and am now seeking a full refund, including my cost of wiring the funds. 

As you allocate your budget, I'd suggest factoring in a decent portion for interior design/furnishings and amenities.

I am seeing a roommate who does not have pets.Cozy furnished 1 bedroom with living room and kitchen privileges, your own private bath and a shared refrigerator.