We have a single family home rented out for 2+years to a tenant and in the beginning of July, we'd hand delivered a letter to one of the tenants notifying them of a $50 rent increase effective this month (September).

but in a competitive market if everyone uses the same ones and didn't adjust the content at all, the results will vary"Actually, if you're using the same content as 50 other people, it's not just that it won't be effective - you can actually be penalized by Google.

Ive heard of horror stories where foreclosure homes were not winterized and a realtor goes to show it with broken water lines in the kitchen leading to a frozen waterfall effect and all the mold and destruction that ensued. 

and with your low interest rates I'm sure the payment is not effecting your lifestyle.

How can I better prepare against these kind of things which would otherwise hinge my LLC acquisitions You talk to someone as smart as @Amy Wan about how not to create a security =), but generally as long as you dont trigger the definition of a security you should be fine.Its something to the effect of having investors who are solely relying on you to provide a return with out any involvement in your project and you're the KP key principal / GP general partner. 

I have found this to be pretty effective.

Effective property taxes in Chicago are for the most part well lower than one will find in suburban Chicagoland, Hammond, Munster, etc.

My understanding is that once DCRA is finished, the rules will get posted for a period of public comment before taking effect.

Simple, flexible, and effective. 

Raising capital is a lot more difficult than I thought and we need to dedicate more time, money, and resources on doing it more effectively.