The energy in person is different for me, and I've made some of my best connections and friends at Chicago meetups.Here is a list of the Chicago event from BP: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of ALL THE CHICAGO MEETUPS that I am happy to share with you. 

As already mentioned, he wouldn't be able to use rent from roommates to help qualify but based on the numbers you shared there should be a VA option available considering how much flexibility there is. 

Thank you for sharing!

While I’m happy to discuss general strategies and best practices, I won’t be sharing additional details about the property’s exact location, nearby city, or financials at this time.

I don't see a smoking gun as of yet, I don't. 

Working with a business partner highlighted the importance of clear communication and shared goals.

Probably go for a 3 bedroom with an office or dining I could convert into a 4th bedroom and shared common areas, would have covered everything with airbnb and still covered most with long term. 

We want to detail the responsibilities, capital contributions, profit and lost sharing percentages, decision-making process, have dispute resolution methods, and exist strategies.

If you remember the coupon or deal you used, please share! 

We do the land up keep and figured in the long run if we can use the other half of our plot for events it will offset any land keeping expense (do not mean anything by this just sharing , faith and movies always say helping others brings good luck.