the last part of that sentence is where the issue lies. you have to get into a habit and routine of putting in the hours for yourself. you have to find the motivation either internally or externally via somebody else keeping you accountable at the end of the day the question you have to ask is "How bad do you want it"? 

The wholesaler was very uncomfortable with this, even though these were mundane documents like lead paint disclosure (with an option to say you don't know about any lead paint). 

Uncomfortably hot.

Some don't care but others are uncomfortable around strangers.

Do they routinely change out cast iron plumbing, aluminum wiring, test for lead-based paint?

To be honest, 30+ minutes on a dirty CTA each way is not something I’m willing to do, I work 70-80h a week (that’s my “little sacrifice” already) so it is important to keep my daily routine optimized, and walking to work from River North/West Loop is not negotiable.That might as well mean that it’s better for me to keep renting rather than “investing” in an overpriced condo. 

They're on month-to-month with long-term tenants who haven't seen a rent increase in years.Have a nine (remaining) day period to gain access (due to tenants), assess conditions, and either continue or pull out of the deal before earnest money is due.The problem we're experiencing is that buying as a package strains our liquid reserves to an uncomfortably tight level.

Maybe negotiating with an aggressive investor is uncomfortable for them, and you put the at ease. 

How can I approach that subject to someone I know without making it uncomfortable? 

Rents are high, we have many clients getting $1300/month for routine 3/1 houses.