@Lynnette E. - Thank you both for your responses.

Download a Schedule E spreadsheet or use Stessa. 

Instead of trading up into new properties or being locked into a DST, I invested the proceeds in multiple real estate syndications. 

I'll be taking all of your guys' thoughts and advice: Getting started no matter what, staying adaptable, building skills and momentum, and @Lynnette E. maybe I won't reach that level of sheer hard work, but I'll definitely be putting in the time and effort!

Make sure that house and at least 3 others in the specific vicinity sells before executing on the sale.

Some other resources I use that are free of charge:Turbo Tenant Stessa (accounting/expense/income tracking)Other investors rather have other paid for programs that included notices/group e-mails, etc...

The home you own in which your parents live will need to verified by 1040 tax returns showing the gross rent and expenses on Schedule "E"  in addition to needing a copy of the lease agreement or rental agreement.

I guess what I am really wondering is if you are you essentially trading potential equity in a home for being able to avoid a seasoning period with the delayed financing route?

@Marquez Robinson I certainly won't tell you what you should or shouldn't do since I don't know you but here is the advice I offered my brother in law when he was in a similar situation getting out of the Navy...Go to a trade school and learn a trade - plumbing, electrical, HVAC, welding, whatever floats your boat. 

My question has two components:Part One: Which metrics to include in the executive output:The current shortlist/ratio's that will make it on my "executive output" are:Capitalization ratioCash-on-Cash ratioReturn on equity (incl. loan paydown, cashflow and appreciation)Debt servicing ratioIs there any metric I am forgetting here to get a first good impression of the property?