It’s a rural area with a huge shortage of housing, regular and student, with a surge in enrollment numbers over the last 5 years.

It could be hard to prove with outside agents (regular buyer agents) as they don't log their clients in on showings, only themselves as the agent.

If you’re referring to a special assessment, the ones for major expenses not covered by the regular dues, then maybe.  

You should only be buying if the regular rate works for you guys.One other note to help you on your journey.

They do it because the contractor asks and they don't know that it's not regular.

Most would be better off with just a regular landlord insurance policy and an umbrella policy.

Folks will generally have a fantastic rental strategy but they don't fit the lense of regular guidelines.

Quote from @Max Smetiouk: Hello Ryan,I am looking to acquire property and debating between regular LT rental and STR rental.

Short term, assuming the real estate lobby doesn't sue this to keep delaying/appealing, once it goes into effect there will be no more broker fees paid by tenant *unless they hire the broker*Some long term effects I can predict already: - Landlords now having to absorb broker fees will bake this into the rent (e.g. how "no fee" units typically are priced a little higher than other units) - Real estate board will require another document (or checkbox) for tenants to sign stating that they're hiring the listing broker and responsible for compensating them for their fee *if* they apply and are approved- Regular New Yorkers will have an even harder time to find an apartment because you cannot legislate/regulate away a housing crises... 

I've seen insurance premiums for flood go up to 5-6k on a regular single family home depending on the area.