(It costs 10k+ to drain, clean, refill the pool so I only do it once an year and this is pretty standard) I think it is matter of if it looks dirty or smells bad when guests use it.

Best practice in cases of broken glass in the pool is to drain the pool.

Appears the guests may have left the faucet "on" when the pipes were frozen and when no water came out, forgot to turn it "off".What may have caused the overflow of the sink is maybe the drain lines were also frozen?

Sometimes I think, well maybe that newby is an expert at draining swamps....or they have a helicopter to reach the landlocked property and want to practice aerial concrete and building material transport.There was a guy on here the other day, challenging me that he could not possibly go look at all the "deals" he was going to buy in Florida for 10c on the $1. 

If they can't do that, keep shopping.This may require digging up the foundation, sealing it from the outside, and installing a french drain to keep water away from the walls.

(Previous rent was $1,300 but we're about to put in a brand new kitchen from the studs, new flooring throughout the house, new furance, adding A/C, etc).So do we just pay for it all upfront and mostly drain all of our savings, or do I let the rent pay for it and utilize our other savings to get a second property this spring/summer to increase our cashflow? 

Most won't insure pools with diving boards or ones without a VGBA drain.2) Include the cost of a pool company to manage the pool in the rent. 

Imagine investing in all new, beautiful finishes, only to discover that the drain pipes are faulty and need to be replaced—an issue that could have been identified and addressed beforehand.

For your part, it might seem like a free roll of the dice to go to court, but there are surprises and landmines along the way, litigation always takes far longer than anybody expects, and the time and emotional expense of fooling with litigation are energy drains on more productive endeavors.

However, I would prefer if the property could support itself and not be a drain on my personal income.