It does take some work and learning but if you are looking to start booking direct, you can take the time.

So why would you NOT take a few hours of hard work and find a solid agent in that area. 

@Daniel Cullen do you have any recommendations for contractors that do quality work and are affordable in the Chicago area?

As for when to call in a contractor, it really depends on the scope of work and your comfort level with DIY projects.

As one of the owners, alongside Peter Vekselman, our goal is to support and guide you through your real estate investing journey.About Partner Driven100% Financing: We cover the costs of acquiring and rehabbing properties, removing a significant barrier for many investors.Coaching and Support: We offer ongoing coaching, deal review, and team support to help you succeed.Profit Sharing: We operate on a 50/50 profit split, ensuring that both parties benefit from successful deals.Comprehensive Tools: Access to software for finding and tracking off-market and pre-auction properties.Real-World ExamplesTo get a better sense of our work and see some of the successful deals we’ve done with our partners, please visit my BiggerPockets profile.

Our first plan didn't work and we would have had to take a loss if we sold it.

Any real estate ventures would be things I consider fun where I can participate in some fashion without doing the bulk of the work and I would derive some autonomy, mastery, and purpose goals from.  

But anything you do is going to take up time, might be a lot of aggravation, and has the risk that after all the work and financial investment, might not pay off to the extent you hope for.

I used the service and wanted to download my work and could not get a live person to help. 

The second property had some light cosmetic work and a new kitchen.