I still have so much to learn and I don't want to come here and just straight up ask for the answer.

I'd love to hear from other more experienced investors who are years ahead of me on what is the first "type" of investment you would do if you could go back and redo this all over?

Because there was one other STR on the block ahead of me, these people knew that a STR means immaculate properties inside and out, and an owner that cares.Let these neighbors of yours know that because of you, this property will always be the nicest in the area.

In all honesty you are trying to foresee the future and the way that SE MI calculates taxes is not that straight forward. 

I would HIGHLY encourage you to get prequalified ahead of time when doing this strategy.  

Meaning, if you're renting for $900/mo and your current mortgage is $700/mo, you're $200 ahead, minus another rental for your family's needs of $900 (assuming you'll be renting same-ish size as one you're looking to rent out now) = -$700/mo so this would be pulled from the cash reserve amount or monthly income amount.

Do I HAVE to have a contractor lined up ahead of time to use these funds as part of my delayed financing?

Or go ahead and attempt to get him out of there?

At least where I am, surrounded by forest, you're in a constant battle with nature to keep it from overtaking your property (that is, it takes straight up time and elbow grease.

Here are a couple that would do it straight in an LLC.