Maintenance and cap-x does not, in large part, have to be a mystery game of wait n see what happens.

As the lessee, I believe you can expense the roof replacement and then wait to exercise your option. 

Oh, wait...you already did, three times but I'm still lobbying to be the first four-timer before @Ben Leybovich takes the spot.  

If you have the means to hold the property, make the repairs to the foundation and wait for up swing in the market, I would try to hold it.  

You don't magically get a tag next to your name that says Cc NOW is motivated.. oh wait... ... wait for it.. wait for it... almost... one more second ...NOW, NOW Cc is motivated, everyone send her a mailer.Silly right?

So for high season, I am always priced higher than my competition and wait closer to season to adjust if I'm not getting bookings.

If you anticipate challenges, it might be strategic to wait until closer to the 90-day notice period required by law.

Then the rest would be the same, except we wait until the morning after check-in to see how things are going since some guests are late arrivals.

Example bids: $400 to snake a drain, $250 to lay an insect trap.* No proactive maintenance, and even the turnovers were inconsistent.

Lay out your cashflow by property.6.