I reached out to proper insurance and was quoted $2307.62 for the year which coming from Florida, was cheaper than I anticipated.

That could make a difference because if you're in a heating climate with a gas furnace that could be cheaper to heat with than an electric mini-split as they become less efficient at very low temps. 5.

@Joe WoodThe distribution from the IRA to yourself is a taxable event.

Can I use this negative cash flow as property losses every year to reduce my taxable income, or not since I make over $150,000?

It is still the cheaper route then going out and buying a house that is probably slightly outdated and not set up how I would like it.

It's a bit cheaper and you will be replacing it in a few years anyway.

Assuming that the units are the exact size, you taxable gain would be allocated 50/50 between the owner occupied unit and the rental unit. 

After realizing I could get the drain tile done quicker and cheaper than what PermaSeal offered, I switched companies.

You might find you get a cheaper price by just asking for a repair and not mentioning the warranty.

It will make borrower money easier and cheaper.