I have a list of them that I can share with you.Chicago, without a doubt, has some downsides, but there are also a lot of positives, like the inventory of older multi-family properties and price points at all levels.Investing out-state can be challenging because of the distance and the need for boots on the ground that you can trust 100%.

With @Michael Baum on this.Another angle of thought - who would have a better chance of success challenging Airbnb TOS:1) A "brand" with 5 units2) A brand with 500 units?

Challenges?

@Deirdre Lizio see a lot of competiting PMCs start with a pledge of doing it better than "what's out there".Always interesting to revisit them 3-5 years later - after they've experienced the reality of challenging tenants AND owners.Look no further than Evernest: they started out with flat fee management at $99/month and promises of better & fairer service & pricing.Now they're at 10%, capped at $199/month - wonder what changed?

It's important to consult with an attorney or an accountant to determine whether an LLC is the right choice for your specific situation.You can reach out to me and my team who can guide you through the process and help you navigate any challenges that may arise.

@Jay Hinrichs @Jonathan Greene @Nicholas L.you have all helped me to really consider what type of challenge / path I want to get into, and all this information is excellent.

Challenges include depreciation in market value (i.e., mobile homes often lose value over time unless they are situated on owned land) and tenant turnover.However, tax advantages include depreciation deductions, which allow you to offset rental income by writing off the property's value over time, and cost segregation, which accelerates certain deductions.

Challenges?

The email was short and challenged us by implying we were looking for investing planning and not tax planning.

I’d love to hear from others who have navigated similar challenges or have insights on improving profitability in the short-term rental space.