I am currently living out of state so I have hired a property management company to handle this task, however, my home is still sitting vacant with very few prospective tenants.

Dealing with non-paying tenants in a state like Massachusetts, which has strong tenant protections, is no small task.

Looking to connect with other working parents who started this business adventure in their early 40's and made it work!

So, if you don't know how to build financial models, there are some available that are pretty good online (adventures in CRE is a great resource).  

Meeting the material participation hours is absolutely doable, even with a property manager, as long as you stay actively involved in key tasks like marketing, bookings, and bookkeeping.

The TakeawayHouse hacking has been an adventure.

After that it is the normal tasks of either turning over a tenant or renewing a tenant.

I can see AI as being potentially super helpful with many RE tasks.

Now, I focus on design and amenities that directly enhance their experience:•Practical Bathrooms: I added a combo washer/dryer to one of my bathrooms because guests coming back from outdoor adventures often need to wash their gear right away.

This is ideal if you have a full-time job or don’t want to deal with day-to-day landlord tasks.✅ Professional Tenant Screening – Property managers have systems in place to screen applicants thoroughly, reducing the risk of bad tenants.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!