I would say do some sort of Break-Even analysis so you can visually see what it takes, how long it will take, and what is required for you to not only replace the lost income and benefits but surpass that level. 

I talked to a couple inspectors to educate myself and they both told me that if there were any areas on the exterior that they couldn't access and they visually observed peeling paint they would have to flag it.

Bathrooms and kitchens are the biggest visuals...new vanity is only a few hundred bucks and will make it pop...shower curtain and rod on high end and it looks so much bettter.

Nothing visually wrong with the building. 

Go with the applicant that you feel visualized themselves in the house during the inspection...did they look at outlet locations?

This really helped me visualize the process of a BRRRR.

Based on your story I don't see that.Second as a home inspector I can tell you that inspection is only visual.

I'm having problems visualizing how to fix up properties to the extent that they need to be, and not overspending to make it beautiful or restore to former glory.

Great looking rehab project @Stephen Herbert - I love seeing the before and after pics because it helps me visualize the end product when I'm looking at property.How did you select the specific staging company?

For those of you who're interested, I completed my ADU project and you can see the 3D visualization of my place here: https://my.matterport.com/models/hRAxQheq93H?