I did the design, permitting, procuring materials, and I was also the GC. 

As many of you know, finding a condo building that permits short-term rentals in Chicago is extremely challenging due to HOA and city restrictions.I just pulled data on a handful of active condo listings where the buildings explicitly allow short-term/Airbnb rentals.

I created a web based software so they can enter the property information and upload pictures.

It seems to be a hot topic lately, with internet gurus like Pace Morby and Heather Blankenship claiming that you can successfully manage an out-of-state RV park remotely by hiring a park operator, cleaning/maintenance staff, and leveraging software/AI for booking, marketing, and guest inquiries.I’m wondering—how realistic is this in practice?

(forgetting to log, categorizing activities, proof for audit, etc.)I’m even considering building a dedicated software/app that makes this easier.Before I dive into it, I’d love to know if there's a real demand and what features would be must-have vs. nice-to-have?

Definitely create a strict late fee policy if you don't already have one and use a software that can auto-apply the late fee and communicate late rent for you.

Even small lots can have say 4 townhouses if the zoning permits.  

Once they have a framework, they free up a huge amount of time so you can focus on strategy and scaling.If you’re running rentals in the Southeast, a VA can easily plug into your property management workflow as long as you give them access to your software (Buildium, AppFolio, RentManager, etc.).Happy to share more about how I structure training and oversight if that’s helpful.

Building permit(s) are required for installations subject to building code(s) and the installation will need to comply with the minimum requirements.

Depending on where you elect to purchase, permitting can take awhile.