From that point, some sort of banking engine would need to be involved that was sophisticated enough to handle and understand trivial to highly complicated financial transactions.In any case, it would be fascinating to a small niche of people (myself included) so not too likely to become a commercial success.

You are way way ahead of 99% of the population, and well on your way to setting yourself up nicely for financial security/independence. 

For a while now I've had a burning passion to strive for financial freedom, experience is the only thing hindering my performance right now.

When one domino falls, they all fall.Like many new investors, you want financial freedom and you want it NOW!

But if the contractor isn't contributing financially and only doing the renovation work I'd think 50/50 would be fair.

I have seen more people torch their retirement plan using this "strategy" than I care to think about.As @Chris Seveney notes, an IRA can be setup with a specialty self-directed custodian so the IRA can be invested in non-traditional assets like real estate. 

I'm just trying to gather as much information as possible and outline a plan ahead of time to ensure that it makes financial sense before I move to the next step.

I’m looking to make this venture both appealing to tenants and financially viable for myself.2.

As a busy mother and devoted wife, you seem to have a lot on your plate in addition to your work as a nurse practitioner and small company owner.If you want to buy your first short-term rental (STR) property, you should set realistic financial goals, specify your investment criteria, and do extensive market research.

Stop looking for "good deals,"....instead focus on buying a quality asset in a quality location.