Also curious how others navigate our short term rental laws (seems like many property owners are advertising for periods shorter than the 14 day minimum) Also curious if many owners are actually paying hotel taxes to the county or waiting for more clarity on the law

This is not a hard law to follow.

If wholesaling were to be banned nationwide, what is your best alternative strategy or next steps to consider?

Until they start to use these new laws and mandates against you.Remember, just a few short years ago, the lockdown and the ability for people to not pay their rent nation wide was crippling small landlords.   

Because of the state's homestead laws, they cannot sue and take the million-dollar home.

I know they recently passed ordinance/laws on ADU's last summer, if I'm not mistaken. 

Although, you and your neighbors may do ok for a while none of you are experts on the current Landlord/Tenant Laws in each state.

Only pay them after they are out and keys are in your hand.In the future, study the law and figure out how to remove tenants without using the court system.

In fact depending on many you have some of the laws don’t even apply to you.

.- Im thinking of not charging security deposit because of all the strict MA laws and just using the last months rent as a sort of security deposit, thoughts?