I recommend my buyers take their tax return draft to their lender to discuss the pros and cons of taking certain deductions.

The "backdoor Roth" strategy allows someone who earns too much income to be eligible to make a direct Roth contribution, to make a non-deductible contribution to a traditional IRA, limited by the annual contribution limits ($5500 for 2013), and then do a Roth conversion by rolling the contribution over from the traditional IRA to a Roth IRA.

I think of insurance as what covers disasters (fire, flood, medical liability, etc) and set my deductible at 5% which makes for a lower premium.

Good morning GP, If your property sells for $300,000, your "net sale price" after deducting your routine selling expenses (brokers commission, title, escrow, closing attorney, documentary transfer tax, etc.) will likely be around $275,000 (ish). 

My assumptions based off research is I will be able to deduct 1/2 of all allowable expenses based off the ADU square footage (My understanding of that list below)  1/2 Mortgage Interest (Not principle) 1/2 Utilities 1/2 Property Taxes 1/2 Insurance (assuming I don't have separate ADU insurance)  1/2 general house maintenance (depending on the issue and if it's related to the ADU)  1/2 Depreciation (Home value, not land divided by 27.5)  KEY QUESTION: If my mortgage (PITI) is $5400, and all of those ADU deductions equal $3800 monthly, and my ADU income is $1800 monthly, am I allowed to pay the difference in "deductions" from my real estate business income? 

Unused passive losses can be carried forward to future years.Regarding your $100,000 investment in a long-term rental property, you can’t deduct the entire amount in the first year.

When you sell a rental property any unallowed passive losses from that specific property are allowed to be deducted against your other income/gains from the property. 

It requires a 1% or 2% deductible and the house must be in an LLC.  

After Operating Expenses are deducted, we're looking at about $13K in NOI.Purchased for cash at the full asking price of $244,900, and assuming NO CapEx or renovations, that's about a 5.3% Cash-on-Cash return.What am I missing?

All of those expenses to keep up the property are deductible from the rent paid by the tenant so they reduce taxable income which directly reduces taxes.