I find myself second-guessing my decisions/strategy/reasoning. 

I second the suggestion to work with a knowledgable CPA or investment advisor when making these decisions. 

Even then, I think everyone starts somewhere, and I’m confident that I would make mostly correct decisions when I do decide to make a purchase.

This should not affect your decision to purchase the property.

There are calculators available here at Bigger Pockets that will help you with your decision and strategy.https://www.biggerpockets.com/...

@Ben Be Congrats on making the decision to dive in!

As a former engineer who decided to pursue real estate investing/agency full-time, you are making a great decision. 

I would still weigh your decision heavily on service- if you are in this for the long haul, you need a relationship with a lender who will go to bat for you!

This will be our first property and we trying to make the most informed decisions.  

Among the factors that influenced the court's decision were the limitations on the co-owners' ability to sell, lease, or encumber either the co-ownership interest or the underlying property, and the manager's effective participation in both profits (through the remarketing fee) and losses (through the advances).