Keep separate accounts for real estate income and costs.

Is there anything I can do to push this cost on the tenant somewhere or is this something I have to pay?

On paper this may look like an obvious solution, however, in practice it can cause more challenges (cost) than it saves for most situations.

I did not do this with two partnerships and one ended in a lawsuit and the other cost me tens of thousands of dollars.

The property hasn’t pulled in a lot to cover the cost but for safety I can manage fixing some within budget. 

Plus the learning curve to invest effectively was too steep to completely disregard it. 

Get with a good agent who understands short term rentals because the more of these you do then you can scale the insurance under a Business Owner Provider Policy (BOP) and then you don't end up with a dozen individual policies out there for each property that cost you a fortune.

But that is rare in today's market with high cost to build

Negative CF is an added cost that defeats the purpose of buying RE. 

Also, assembling your Core 4 Real Estate Team is crucial for navigating the process effectively.