Automatically add money to an S&P 500 ETF into your Roth at predetermined periods spread throughout the year to surf off both gains and losses.

This lets you run any report you could imagine, including a Profit & Loss by Class (property) so pretty handy.  

I received a landlord dwelling quote from Travelers for Coverage A - dwelling for $223,600 plus 25% of additional replacement cost coverage which puts the total at $279,500, plus $28k for furnishings and $70k for loss of use.I understand I wouldn’t need to purchase the land in a rebuild, but $280k seems low for a cabin worth $520k, not to mention the risk of inflation continuing to drive costs higher for building costs and labor.

Last year was easy to claim a loss and maximize my tax benefits because I only collected a half month of rent and spent far more than that getting the place going.

Setting the rent, in this case, would be a bit of a challenge, as a fair rent would find some sort of balance between the risk of a loss if the STR experiences low occupancy and the reward of making more profit should the occupancy be high.  

As an investor with a smaller portfolio I really put a lot of weight on Cash on Cash Return. 

You have a couple of long-term rentals with mortgages, and they already show a net loss with the "slow" depreciation.

If the market bobbles and your ARV you calculated in the beginning isn't possible at the time of sale and there is a loss, they are likely going to be experiencing a percentage of that loss as well. 

My uncle personally has a few cash flowing rentals that at the time of purchase he got at a good price before major market changes, and even through the overall loss of value in his doors they still maintain a higher growth potential just with the cities intense influx of people, organizations, sports teams ETC...Hope that's in some way helpful!

This is particularly common in two situations: pets and parking.With regard to animals, pet rent is usually charged based on the size and/or weight of the animal.