I have a good idea of how I want to get there, I’m just curious of other people’s paths to get there.My original goal with real estate was to provide additional income for retirement; have a couple paid off houses and help supplement retirement income from my 401k, social security (if it still exists), etc.

You might find that kind of service with a bigger firm for which you'll pay accordingly ($$$$+ annually).You need to learn yourself or pony up the money - here are some books to get you started on this:for accounting and taxes - Every Landlord's Tax Deduction Guide 15th Edition (and you can supplement that with Deduct It!

I have good capital and a supplemental income from a property I inherited in Virginia.

I work full time and like many of us here, I am looking to supplement my income and eventually not be 100% reliant on the 9-5.

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.