If you're open to expanding your search, Columbus OH also has positive cash flowing deals at an affordable price point - $120k-$180k. 

I’ve had to widen my search radius to smaller suburbs or target properties needing light cosmetic work to make the numbers work.Value-add opportunities: Adding amenities tenants love, like finished basements or upgraded kitchens, seems to justify rent premiums in this market.Navigating the competition:Be creative with financing: Seller financing or partnering with other investors has been helpful to secure deals when conventional offers didn’t cut it.Work with local agents and wholesalers: They often have their finger on the pulse of off-market opportunities, which is critical in a hot market.For those new to suburban Chicago investing, I’d say the key is finding the “sweet spot” neighborhoods—ones on the rise but not yet maxed out in price.

I think you can probably search for anything and with the right key words get the results you're looking for.

I am also in search of similar resources in that area.

Emphasize how this arrangement could work to their benefit, offering steady income, avoiding a traditional sale process, and giving them the freedom to move forward with their plans such as buying that sailboat and sailing around the world.If they ultimately decide they’re not interested in selling, you’re still in a great position to continue your search and buy your own property in the near future.

In the past when I am looking for a property manager I google to find all managers with physical offices in close proximity to my properties to narrow my search and ignore all sponsored adds that fake that they are local.Since you have self managed, you will be better equipped to "manage the manager".

I invite you to search this forum about ADU appraisals.  

The public searches are pretty limited in scope for a true investor. 

You may have to search a bit for the right contractor or engineer - sometimes I see one solution dominating in an area - "that is how we always do it" 

figuring that if I track and work towards creating and "presenting" 250 specific deals to my clients.My Theory being: Tracking "deals presented" will pull forward the need to go search and find deals, and will also drive the deals closed and revenue numbers, so we shall see but logics out to me so I'm liking it so far.