However, I feel like I am just bleeding money.

Rising rents is going to stir the pot.

Because they will get defensive if they feel you are pressuring them.

@Andrew Foster some decent advice here, but also some feedback from those who really don't have enough info to support their perspective.Many DIY investors price repairs on materials only and forget about labor as they do their own work.We're a PMC in Metro Detroit, but here's how our process would work:1) MoveOut Video & Pics used to create Scope Of Work (SOW)2) SOW broken down into Priority Categories:- Health & Safety- Government Required (municipality/S8 inspection requirements)- Property Preservation- Marketing Impact / Tenant Retention- Miscellaneous3) Bids obtained if we feel work will exceed Owner Approval Threshold4) Bid sent & discussed with owner to, "redline to their budget"5) Work begins once owner approves & funds6) Completion video/pics providedOf course, while this is going on our Marketing Dept would be doing a rental analysis & ad, and discussing with owner.

Because of the low maintenance I feel bored.

The activity and the buyers and builders talking will help stir the pot.  

The only feeling is relief.

I've been at it for a year and I still feel like its a struggle. 

@Chris ChaffinI can relate to how you’re feeling!

I have informed him of this and he said he just "doesn't feel comfortable" now.