I would lead with what the draw is and what sets you apart from your competition.

If you have the money set aside I would swallow the pill now.

Assuming you already paid for the first occurrence, if it happens again and the plumber doesn't find anything wrong then, yes, the tenant should be responsible for the invoice.Your PM should be setting those expectations when they communicate with your tenant."

However, I also think that a lot of people who set out to pursue this strategy miss the fact that it is literally a lifetime commitment to deferring taxes, which by definition means not realizing the gains.

With your VA benefits and tax break, you are really set to do exactly what you want.

Like @John Underwood mentioned, you need to set the expectation of a 5 star review.We're very specific on our messaging automation. 

We use a conversational AI and appointment setting platform in follow up, outbound, and after hours lead intake.

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

It is more complex and has added requirements such as a formal set of books just like a corporation. 

A good freind of mine set up an STR in a similarly lenient area and found that they could focus much more on guest experience rather than the administrative hassle.