Obviously I want to reduce my cost of financing, and with Investor loans even more expensive I’m looking for other options.

I'm also planning to reduce my deductible to $5k once I get the new roof on. $10k always felt a bit high even though I always keep at least this amount in reserves.If the insurance company declines to help pay due to the age of the roof, I may just set some money aside specifically for the roof and then replace it later this year or early next.

We're definitely going to do our taxes first and see how things shakeout there first with a conventional loan since we do have W-2 income to support a regular mortgage, just wasn't sure how over time these expenses writeoffs start to reduce your buying potential with conventional loans. 

If an investor that is local to your property makes a recommendation, it still may not be foolproof, but it reduces our risk. 

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.