In my experience reliance on trusts for protection is highly misplaced. 

you can roll that small charge into the rental price so that you are not paying it, the guest is,  ....... if someone is on google maps looking in my area, my location will show as a rental with a link to my website (yes, i have gotten some bookings that way also). it sounds like you are giving an opinion on something you have no personal experience with (i could be wrong), so some of your "facts" are wrong or misplaced. ....I think we're all just speaking from our personal experience.

I also did get a separate credit card to use just for house expenses.This makes it a whole lot easier, especially if you misplace a receipt when doing taxes.

In many cases the light source was an added bonus but today, unless the bathroom is really designed appropriately for having a window, it is most often is misplaced in a shower/tub set up. 

If that is not an option, I would suggest LTR, MTR it through insurance agencies for misplaced homeowners, or just selling the property.

Quote from @V.G Jason: I think the moral of your story is a bit misplaced.

If the roof was new when bought, there may simply be a little section that needs attention. maybe a misplaced nail, or maybe wind ripped off a shingle. flashing? 

Hmmmmm....seems I misplaced the link, I'll have to call on Joshua Dorkin or Brandon Turner to provide that.

Things like power outages during winter storms, septic clogs due to misplaced products into the toilet have been the biggest issue.

Depending on where in NYC the property is located, the building can be old enough so that it has no official CO on file (this happens when building had original paper documentation but the city lost/misplaced in moves, fires, damages, etc.) - this is something that the title company will dig out.