I've asked myself these very same questions and don't feel guilty ordering what I want off the menu anymore.

Even if I were sued, I document everything and obey the law, so I won't be found guilty.

But then I felt guilty about taking them up on it because am I really providing enough value to justify charging for that time?

Every business in the world must be run by immoral people with the way inflation has been increasing.People who feel guilty about increasing rents are in the wrong business, or should have someone running their business for them.Failing to increase rents for a single-family home only takes some money from your pocket, but failing to increase rents for multi-unit properties causes landlords to have properties with rents below market value and when those landlords sell their properties they tend to lose tens of thousands of dollars because the value for multi-unit properties depends highly on the annual gross income.We raise rents for every tenant on the same month every year like clockwork because we are running a business and our good hearts, feelings and worries about other people's problems are not factors we take into consideration.

Why do Landlords always feel guilty about increasing rates to keep up with the market?

The power company does would not text you or plead with you if you did't pay on time. 

Could be Big Brother keeping an eye on you, because we're guilty until proven innocent by paying money and submitting to their heavy-handed regulations.

The price is driven by the market, not you, and you shouldn't feel guilty for charging what something is worth.Once you own the property, you notify the tenant immediately that you will not be renewing their lease in November because you need to "do some work" and then get it to market rate.

However I'm hoping to be a passive investor so figuring that out as a service for others doesn't sound appealing to me :p  On a similar note, I definitely feel guilty about evicting people, but with 10 or 20k given to them in cash, why not buy their own home with that??

Even if I were sued, I document everything and obey the law, so I won't be found guilty.