You want to invest just to have a place to live and potentially offsetting your mortgage payment by renting out the vacated rooms or having x amount of cashflow in the future?

It also really helps to have an experienced VA lender on your team like @Zack Karp who can help you avoid & navigate potential problems.

Billboards are new animal to us & their potential is a gray area to me. 

It is potentially possible that a scenario would not get automated approval through Fannie's automated system call Desktop Underwriter (DU/DO) at 75% but would at 70% but again if that was the case it should be explained that way.  

You want to have a discussion whether the property is considered 'active' or 'passive'If it is active, you can potentially accelerate the losses to offset your other forms of income.

You can have a lot of social security, rental income, interest, dividends, etcI am not to say your income will be higher when you retire or that tax rates will be much higher, I am just here to say the only difference is 10% and not 30%.To add on all of this - If you keep your assets in a retirement account, your distribution will be taxed at marginal tax rates(Currently tax rates are between 10% and 37% + state taxes)If you invest personally in your own name, you have the opportunity to escape tax on any appreciation if you have heirs that inherit the property.Even if you decide to sell the property, you are paying taxes at the preferred capital gains tax rate(Currently at 0%, 15% or 20% + State taxes + Potentially NIIT)That difference alone pays for the 10% penalty.

Good area with value add potential and poor previous operations/management.

Is there a tool to use to determine what the highest potential disasters are? 

What information about myself and my partnership can I pre-package to arm myself with before approaching a potential lender?

So basically if I’m understanding you correctly, your saying a way I could potentially use my equity is as the down payment on a BRRRR as long as it’s ARV was large enough to get my HELOC money back after refinancing?