Early retirement, reduced work week, financial freedom, etc. 

We did it, and they reduced all the fines if not negated them.Just tell them you were unaware and explain the situation to them.This is a great reason why I recommend that owners keep city notifications coming to them directly.

If I buy more time by reducing rent for the winter a bit (let’s say $50/month) $150 would be way less costly than the cost of two baseboard heaters, the cost to set them up and to run them. 

When you take deprecation (or, even if you don't but should have), the basis for the property gets reduced.

The deduction is taken over the course of the depreciation period, and the amount of the deduction reduces the amount of taxable income.

@Frank Greg yes, they did, and I am sure that is built into their projections for reduced inflation.

Just curious if I can reduce my personal tax liability with the purchase of a vacation home, or if I should just treat this the same as my other LTR investments and capture everything under the LLC. 

In various areas I'm seeing rental % increase caps, 90 day notice for increases, banning or reducing application fees, reducing deposits to 1 month rent. 

So, even though the house flipping isn't super tax-efficient, by investing in tax-efficient things like multifamily, you can drastically reduce the net amount you'll pay in taxes.

Everything is negotiable.You can reach out to her and request that she forgo the fee or ask her to reduce it and see what she says.Is she a good agent?