This eliminates the problem of increasing your debt and damaging your credit score.

Also, you will likely only be able to use the rent to offset the mortgage pmt debt on the rental property to $0 since you dont have any Sched E history yet. 

That all makes sense to me but it makes me wonder how can you be "financially free" or even just start building wealth if you are 100's of thousands of dollars in debt at all times.

To defer all of your gain, you'll want to trade up in value, replace all the debt (meaning new properties have at least $350,700 of debt), and not take any cash from the exchange (this is boot which = taxable gain).As for replacement property, it just has to be real property - meaning it can be commercial, STR, land, etc!

Quote from @Monty Alston: Quote from @Travis Timmons: You need more income, not more debt.

Additionally, since my parents are nearing the retirement age, I'd like to prioritize low-debt, high-cashflow deals.

Having a lease in place will help you as well - some lenders won't refi a vacant property.For your refi, you're usually looking at 75-80% max LTV with a debt service loan.

Of course, with private lenders, you must give up equity or a return on the debt. 

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

we did the first 3 in a 18 month period we used internal funds so no debt.. these were 350k to 400k all in projects.. so U need cash to be a spec builder or you need investors if you dont have cash..