From podcasts to forums, you’ve all helped me learn, save, and build the confidence to take this step.That said, I’m reaching out to ask for advice.

Managing tenants is no easy task, it takes such a wide skill set. 

Take a look at BP's blog where new articles are published every day: https://www.biggerpockets.com/blog4.

I am trying to assess whether I should take it solo , leave it or scout an experienced partner.

Now, moving forward he offered for us to take it over completely.

They can help you navigate the market and avoid common pitfalls.If you’re serious about taking the plunge, start analyzing properties in both Boston and Chicago markets to understand local trends.

Some PM companies take on higher end stuff (think Cul-De-Sac neighborhoods) and some focus on the hood.

@Wale Lawal This is great advice, and I’ll definitely take it to heart.

I always tell clients to take care of the hard job first - If this is a sellers market then find your property and even get it under contract before you sell your old property.  

Be skeptical of the developer's claims, as your property's value likely won't see substantial growth until the entire development is completed and sold, which could take several years.