When I ran the numbers for both units filed with tenants the profit cashed flowed great, but with me living in the property it didn’t cash flow: not by much.

If you pay them more than $600 this year, you'll need to get a W9 from them so you can file 1099's next year.

Sometimes an LLC will have only one member and choose to be taxed as a sole proprietor which means that it does not file it's own tax return. 

After standard deduction 24,800(married filing jointly), I have a negative taxable income of -24800 which is same as 0, meaning I don't get any bonus points for having large negative income.

It will save you money and also be easier to file your business returns at the beginning of the year because they're the most familiar with your business.

It allows me to quickly file all my receipts by category and project and generate expense reports easily.I've heard (from the company) that BuilderTrend has some robust functionality in this area that is specifically designed for contractors and builders, and could be worth an investigation if you find that a more generic expensing setup doesn't suffice.

If you need to pay for a new kidney....These are legitimate reasons to sell and pay the tax.Tell him to stick to filing out 1040s. 

Confirm with local water authorityLawn care/snow removal: $50-150/month depending on location and property specificsOther shared utilities: Property dependentTrash removal: Property dependentPest control: Property dependentProfessional/Admin fees: $25+/month depending on the size of the property to cover tax filings, advertising, etc.

This is my only income in Colorado.Does anyone know if I still need to file a Colorado state tax return?

Dont let them file for eviction, even just the filing can cause problems finding housing in the future.