My state allows me to charge a late fee on the 5th day of the month, so that's what I do.

Reassess your path and timing, if its truly the ONLY thing you want to do in life, then get a job working for a commercial developer or an investor who buys frequently.

Charge the tenants a higher rent rate and include utilities with their rent.

I’m on the west coast so pools are often a selling point and can charge more for this feature.

I work it into what I pay for the property and what I charge for rent. 

However I did find that HRB charges a fee for every W-2, 1099, and P&L as well as any other form you gave them when preparing my taxes so what was once a $300 tax prep had turned into about $1700 the last year he did them.

., two of the markets that I frequent are mostly 7-day minimums during the high season. 

The current version of the ATCP you are violating is ATCP 134.08(4), which prohibits the same exact thing as 704.44(4m) prohibits…the kicker being that the ATCP (the consumer protection act) comes with the added penalty of you being charged double damages and actual attorney fees because the act itself is promogulated under Wis.

Because of this, they have changed their fee structure on me two times in the past two years2) They don't have back up cleaners so when the cleaner can't clean, they block off my calendar3) They do not have easily legible financial statements and do not provide 1099s 4) They have made decisions that have required my money without consent5) They block off check-ins on Sundays6) They are not great with technology - though they try to use hostfully to list on many platforms, I will frequently see that my listing is not up on VRBO for example.

@Kaushik Kahlon there are several services that will charge the tenant, not the owner.Innago, is one.