You might be able to go this route if your lease says something to that effect.Without lease support, you can write them a letter informing them they are in violation of the terms of their lease due to the lack of proof of insurance.

If you want to violate them thats your call. but since your asking sounds like you want to follow the laws which I support and would recommend.

As I mentioned before, one of my main reasons for switching was to get connected with Marriott Homes and Villas, so that really narrowed my options down to PMSs that support that integration.

You could start with your agent or a local agent who supports investors and could have contacts to refer to you.Lastly, you could consider negotiating with a local PM to take on a hybrid approach to management.  

Your question has been debated between BP tax experts both privately and publicly, for example here: https://www.biggerpockets.com/forums/51/topics/819991-expens...And we ended up where we started: no consensus and no clarity.There have also been court decisions that support my interpretation, even though I personally find these court decisions debatable.

Start small, be patient, and stay connected with local meetups and online investor communities for support. 

I had scraped and struggled along until then and I was just exhausted from the transient nature of the “gigs” I used to support myself up until that point .

Most people like to figure it out themselves but lack the support or knowledge in all parts of multifamily investing.

Additionally, most servicers will provide the tax documents needed at end of year (1099-INT, 1098-INT) and can also issue notices of NSF, late payments and support delinquency /default.

Stessa support has so far been unhelpful.