If in the rare chance they do allow short term rentals in the HOA rules/regulations and association documents, don't be surprised if they change that ruling after you buy. 

- Any lessons learned or best practices you’d recommend for someone leaning toward this approach?

Here you go: https://dicksonlawgroup.com/practice-areas/landlord-tenant-d...The biggest difference between eviction attorneys is pricing.

They might be fine managing new construction, but I have seem MANY investors almost tank from their fee schedule on managing older homes...i would compare it to almost predatory practice.

Is it a normal practice to have a deal set up where you find a new place for the seller to move to?

Ensure you understand local regulations regarding permits; it’s usually a good idea for your associates to form an LLC for liability protection, but individuals can do renovations as long as they pull the necessary permits.

I'm not sure which places are best to focus on with rules and regulations getting strict in some places. 

In practice, this could mean 5 extra days that no rent is collected.  

Hey @Caprice Watkins, so Sheboygan does have some STR regulations. 

Research local regulations thoroughly, as towns often require permits, owner occupancy, or restrict rental days.