However, a few have had enough merit that it may have caused stress if it were not for the umbrella coverage (for example evicting a tenant with ESAs for lease violation of repeatedly introducing ESAs without following the process in the lease).  

With a young kid and 9-5 job, may not be the best time to move to a different state but I do heart you on the merits

TL/DR:  Anybody have any perspective on the relative merits of national v. regional self-storage brokers they can offer me? 

Other brokers and I have an ongoing debate about the merits of flat paint vs a paint with a sheen but in my experience flat is the way to go.

Adam,1) Based on your office building, the location & market list the potential tenants who will love your office building.2) Seek out through LinkedIn people who work for those prospective tenants3) Connect with those people and ask them if they want a newly renovated office space in Chicago4) Email them with a professional looking package that sells the merit of your office buildinge.g., say one of the tenants you identify is Procter & GambleUse linkedin to search for P&G people who work in their commercial real estate department (or people in charge of looking for office space)

DSTs are a unique beast in and of themselves, so it would merit a deep dive into them if you're truly keen on DST investing.In simplest terms, the relative benefit of a DST over a multi-family investment is the simplicity and tenant class. 

It's important to consider the local market demand, regulations around STRs, and how these locations compare in terms of potential rental income and growth.In summary, both strategies have their merits.

Most of Cleveland natives will do anything it takes to avoid East Cleveland, to the extent where I'd say people are blowing it a little out of proportion, but there is some merit to it.

Although there might be some merit towards being active now just in the "slower" part of the real estate activity calendar (Winter) than summer which is more likely to be elevated from a price standpoint 

The boost in self esteem from earning something on her own merits can't be overstated when she's already going through a tough time.