While the owner is free to sell the property and the information about how they run it as a business, AirBnB does not allow them to sell their online identity for the platform.

I am actually starting a Reverse Trolling Coaching Coaching program, and I am just Reverse Reverse Reverse Trolling right now.

Luckily, I did not include this unit in my underwriting when purchasing, so the survival of this property is not contingent on this situation.Continuing to optimize for management of the building when I move out, like moving everyone to online rent payments or adding remote accessible security cameras.Exploring opportunities to expand my portfolio—I've begun my hunt for my next 3 to 4-unit building to house hack, ideally in Lake View, North Center, or Ravenswood.This year taught me that real estate investing isn’t easy, but it’s undoubtedly worth it.

The only 110v dryers I see online are small portable units.

You can find online mortgage calculators that allow you to play around and see what happens if you do an extra payment or increase your payments.

This is expensive but you'll have a place to work and meet with people when you're in town that matches your online presence.

Are there specific military programs or contacts I should look into for housing opportunities?

I have found some information that might be helpful John.There are government backed programs like Fannie Mae Homestyle Renovation Loan and Freddie Mac Home Possible Renovation Loan, in addition to the FHA 203k loan. 

And you'll have the best rate/points options with a primary residence.Option #2 is great, especially if you're willing to move into one of the units (because the down payment minimum is just 5% or 3.5% depending on program), but as you mentioned it's really tough here to find small multifamily here.

Some towns require a nightly online form to be filled out for any non-residents who are parking their cars (this is easily automated from an operational standpoint).As the MTR market becomes saturated over time, those who have separated themselves from the rest of the "competition" will continue to perform well by having an outstanding listing and all the MTR-specific amenities.