My primary concern is if these supports weather another 20 years in the ground like they currently are.

To keep pouring during cold weather they can add hot water to the mix.

I think it's unlikely the tenant will pay the buyout fee (she's already resisting) but you should definitely push her to do so since it's included in your lease.

The street frontage improvements the city required like curb and concrete approaches are waiting until next year because of the cold weather.

You want Taxable Income (2) to be as low as possible.You want Net Income (3) to be as high as possible.You want Cash flow (1) to be as high as positive, but if you have a lot of money saved up to weather the tough times then it isn't strictly necessary.Net Income (3) is the single most important measure.Your cash flow is mostly important for knowing that you can pay your obligations as they come due.

Also, even though the weather is typically "better" in Maui during the summer (less rain), people typically want to visit Maui when their weather is worse where they live (winter).

The idea of an STR attracted me as I could do it somewhere with good weather, I am sure living in MKE you know that it is not a great market for STR properties.

It's a great strategy in LA, especially considering the resistance to short term rentals here.Allen

I do not think anything new would be said but the weather is nice here in the winter you may enjoy that.

When landlord goes to get the home ready for the Cert OF Occ inspection, tenants allow landlord entranceand there are no signs of tenants leaving (no boxes, no packing starting etc)Note - during the entire process, there was no indication of resistance from tenants.