That stuff I can hire out more in the future but I am choosing to put more of my maintenance budget in my pocket for now. 

Here's why some choose bricks and mortar:Tangible Asset: You own a physical property with potential for appreciation.Leverage: Use debt (mortgages) to magnify your returns (not possible with stocks).Passive Income: Rents provide a steady income stream (dividends are not guaranteed with stocks).

Why would companies choose to set up new operations in a high operating cost city?

Tenant screening is challenging and you have to have the right process in place to make sure you choose wisely.The main thing as many said, this shows a red flag on the amount.

We choose 20% since we would be out of state / wanted to be conservative but can adjust downwards.

Unfortunately, this is the end result in many instances when purchasing in lower barrier markets whether through a turn key provider or on your own  and the question of who will buy this property when you choose to sell is rarely given the time it deserves. 

Some of these renters are capitalizing on low interest rates and choosing to buy, but many are unable to buy due to lack of down payment or credit factors. 

For LTRs, prioritize markets with population growth and strong job markets.Wherever you choose, work with an investor-friendly agent who knows the local market and can help you analyze deals.

Quote from @Fakaradin Floyd: @John Underwood I would love to do this but where I live sadly there aren't any lower end inexpensive houses I've already tried this and have put in over 5 offers for houses and lost to bidding wars everytime hence why I'm choosing this strategy. 

Be prepared for trial runs with several different candidates if you choose to hire a handyman to make sure they turn out to be qualified and dependable.