He showed me a box of nails he used, and explained the gutters got loose from the wooden frame, so he took them off and re-nailed it with longer nails.

I'll take an aged port in a 200-year-old masonry wine grotto over a margarita at a tiki bar. 

Kitchen countertopsGranite is a classic provided you seal it in case someone spills red wine. 

@Javante Wooden Connect with @Matthew Schneider he can help your REI needs in those areas 

We added a privacy fence, made it an open concept, and made the property pop with a wooden beam and open shelves.

If this is a wooden structure, you may want to submit a claim to your insurance if the damage is a long term spread of wood rot.

Are they old wooden windows that are in good shape or need a ton of paint and TLC?

The wine country is very upscale. 

If you have a giant, old, wooden house you will need to budget for a lot of ongoing maintenance that will be painstaking to do yourself and expensive to pay for. 

But all the wining in the world will not change the facts and as such, your tenant needs to pay the increase or find a new place to live.That said, a $400 monthly increase does seem steep all at once and quite frankly, it was your own fault for not raising the rents in smaller increments each year.