A lot of properties here need some level of work—sometimes it’s just cosmetic upgrades, other times it’s mechanicals or kitchens/baths.

"Upgrade your Nashville home with beautiful hardwood floors from Willow Flooring.

They took it upon themselves to buy and replace the broken one.

You can delay upgrading the TV size as you planned.

1) the cost of upgrading liability from 250k to 1 million on a dozen properties is waaaaay more than a 2 million umbrella. 2) you are 10x more likely to hurt someone with your car or personally than have them hurt at your rental property.

If I did this method then it would be a good time to do electrical upgrades and add insulation (seems to be the most expensive by far). 

No additions, upgrades that increase square footage etc.

This relationship is broken beyond repair.On the bright side: you have to deal with a situation like this sooner or later, it's part of the biz.

We upgraded our website at a cost of about $2,000; we initiated a SEO program cost of which is $300 or so monthly, and we initiated an email campaign cost of $275 monthly.  

They should also do the upgrades you recommended, but saying that $1800 is top of the market is incorrect.