With that same down payment amount I could buy multiple multifamilies in an area that actually cash flows and keep living where I want to live. 

Here's a few things you might want to consider:Open Family Discussion: Since there are multiple heirs and not all are on great terms, it’s important to have an open conversation with everyone involved.

You can have multiple base stations and multiple properties all connected under one account. 

Get multiple quotes and don't go with the cheapest guy.

You can find monthly market updates for Milwaukee on YouTube.Quality investment grade duplexes between 250k and 450k sell with multiple offers on the first weekend, usually 2-5% over list price. 

Ensure you have a detailed renovation plan and consider obtaining quotes from multiple contractors to validate this estimate.Rental Estimates Your projected rents of $2,000 and $2,600 seem promising.

Personally I would probably just multiple by 0.005 if you're gonna use this as I feel like Zillow always estimates low.But I personally use instant Steadily Insurance estimates inside BrightInvestor - those do vary their estimate by location, unit count, stories, year built, etc.

Short-term rentals could offer strong returns, but consider how much management effort that might take, especially with multiple properties already under your belt.

If I had hired a pro, it would have been done in under two and the extra rent income would have paid for the pro.My biggest misconception was my limited belief that I couldn't buy multiple investments.

Multiple times projects took so long to get started or to get an appropriate bid, I ended up having to handle it myself (ie. roof replacement, unit turns, etc.)