The cons as i see it include loosing the 2 of 5 year cap gain exception, typically not an ideal rental because the emphasis at purchase was buying a good home for your family and not a rental with optimal return (my ex-home consistently has the lowest cash flow for equity in my RE portfolio), not disconnected enough from the property causes addition angst on damage and may result in over improvement.  

Meanwhile your website lists 11 staff members with the following titles: CRM/Email manager (1); SEO Manager (1); Content Creator (3); Director of Advertising (1);  Digital Advertising Specialist (1); Event Logistic Specialist (1); Chief Creative Officer (1); Social Media Manager (1); Senior Social Media Engagement (1)How is this overhead optimizing your real estate portfolio so you can return to making distributions?

But it’s not everything - this software is optimizing for the host’s success and not balancing that enough with the guest experience.

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.

Cash flow can absolutely replace your income, but it’s rarely immediate or without effort.The truth lies somewhere between the podcasts’ optimism and the meetups’ cautionary tales.

Another good read is Optimize Your Airbnb By Daniel Vroman Rusteen.

This approach mitigates risk while leveraging your resources effectively.Looks like your household could qualify as REPS and really offset your taxes if your portfolio is optimized.

A private lender is optimal (so you don't have to use all of your cash and can scale easier if desired) because you may not have to jump through as many hoops.

Real Estate values, nationally, have never decreased over any 10 years. https://fred.stlouisfed.org/series/MSPUSFocus on optimizing active income first.

i have 4 STRs that i use professional PM, 2 of the STRs, after expenses including PM, are not outproducing my LTRs.For optimal ROI in this market requires a value add and quick, at least partial, exit.