It's a tough job to manage a property well which is why I outsource all my property management.

Do those things in real estate, and outsource/ignore the other stuff.  

I should've outsourced the upgrades, and day-to-day management.

Too expensive to work on rental properties.Type 2 (High Quality, Average Price)They rarely do new construction (except for garages), focus on additions & remodeling, no maintenance work.Often online advertising, may have one-person sales/bid staff, outsources design, office support typically consists of secretary and bookkeeper.Equates to a decent amount of overhead, leading to markups of 35%+.Bids: May take a while to get a bid from them because they don’t have dedicated sales staff.

Your time is worth something and eventually you might want to outsource the management. 

If you’re in Cleveland start there and then outsource and grow into other markets.

If you want to outsource it completely, that's easier.For vendors, consider a lockbox if you want them to have access. 

Did you automate/outsource these methods or do you do much of it yourself?

This is why it is recommended that you outsource property management to an impartial third party. 

The reality is, most people don't end up needing anything more efficient because they eventually outsource to a 3rd party property manager.