You could prolong your financial suffering and continue to supplement his rent but your best option would be to go directly to $1550 and stop losing money.

Our long term goal is to build our portfolio and gain passive income to supplement our full time jobs.

Having great return does not mean we supplement tenants rent and throw money away.

You can try seeing what the insurance company will offer and if you're not satisfied, you can retain a public adjuster to pursue a supplement. 

My problem is I don't have a high-paying job to back into like a lot of investors on BP and my only other passion is a career with low earning potential (film directing), so I feel like adding value through doing my own work is a great way to make this a full-time gig sooner than later while maybe supplementing our income with part-time work or start contracting for others once I get more experience.

Now, down at those temperatures, your COP will be approaching 1.Here where we have cold winters, code requires an ancillary heat source - electric baseboard heaters are most commonly used - to supplement the heat pump in the dead of winter (we frequently get 2-3 weeks where temperatures are below -20C).In a warmer climates, even if code requires you to put in ancillary heat, you should never have to use it.

And for those who want to retire early and tap into retirement account to supplement their income, there are ways to do so, here is an article explaining the details:https://www.forbes.com/sites/forbesfinancecouncil/...The bottom line is this: even if you have to pay the penalties for accessing retirement funds early, because you are able to grow them tax-deferred you'll be better off investing inside of a qualified plan rather than using taxable account. 

So how is it that these world record-setting athletes, who are more or less following similar programming to the rest of the world, taking similar supplements, and have the same 24 hours in a day that you and I (and the rest of the world) have, are predominantly from a select few Asian and Euro countries?

Targeting a duplex since the goal is cash flow and supplemental income down the road - would invest in a SFR though too. 

Reading can always be used as a supplement but it’s important to start taking action and avoid getting stuck in the passive education cycle.