He is now "claiming" that he took a $70K loss but has not provided any documents. 

A few basic ideas that I think could help: 1. tax loss harvesting2.

I've had several wins that way; nice as it offsets those losses that are bound to happen with repair expenses!

It included similar "loss of rental income", same liability limits, included building code upgrade, vandalism and even 10% for water damage and 5K for rot.  

This creates two loan payments ($100,000 of equity and $300,000 on the new mortgage).Key NumbersHome Equity Loan Interest Rate: 6%Mortgage Interest Rate: 7%Rental Income: $3,000 per monthExpenses (management, taxes, insurance, maintenance): $800 per monthIncome and ExpensesMonthly Rental Income: $3,000Monthly Expenses: $800Monthly Mortgage Payment: $2,000ExplanationThe investor earns $3,000 in rent each month.They pay $2,000 on the investment property mortgage and $800 on other expenses.This leaves $200 profit each month or $2,400 per year.However, you have to pay $6,000 interest on the equity borrowed.This leaves you with an annual loss of $3,600.This example shows that while the rental property generates positive monthly income, the interest cost of borrowing the initial $100,000 results in an overall annual loss.

I hear there's a lot of potential to make some great deals as a buyer/investor on homes in Chicago because of the significant net population loss over the last 2 years. 

Because of these risks, second-position loans often come with higher interest rates and stricter terms to compensate for the increased likelihood of loss.

In short, if you're not renting every week of July-August and every weekend of the winter, you're taking losses, particularly given the ridiculous prices I'm seeing new investors pay farther north in vacation areas like North Conway or the White Mountains.And looking solely at North Conway's recent court case is a red herring: plenty of small towns around the NH continue to enact knee-jerk reactions and excessive permitting/regulations as a reaction to STRs assumed role raising housing prices and shrinking supply for local residents.

fha. 3.8% interest and Currently owe 450kMortgage $3,400.00Currently we are renting home out for $2,400 and taking a lossLiving in an apartment for $1700 making total living cost $2700 with the 1k for covering loss on home Household income 180k-200k Please help me figure out what makes the most sense in this situation.

First off i wanted to say I'm sorry to hear about your loss.