I think building equity through the rehab itself and then house hacking each room would give me the biggest avenue to maximize savings/equity for that potential second property. 

they are more expensive than stick built take years to get approved through the building  departments in many jurisdictions and the folks that buy them are eclectic to a certain degree.. they work well in Rural settings where you can really lock them tight and leave and not worry about thieves.  

I am a real estate agent that has access to the MLS, but I've seen through my research that the best deals are the ones off-market.

I absorb information very fast and have gone through a good chunk of course work and books in just a short time.I am ready to start looking for deals.

I'm using sites like airdna to help analyze deals but would like a little tip on how to navigate local licensing (if needed or not) and how I could maybe start one in Madison specifically what hoops I need to jump through?

I am currently going through the same process during my due diligence on a Quadplex.

I sent the LOIs through Crexi for several of them and through email for a few of them.

We purchased it the traditional way by going through an agent, we viewed some houses on our second trip out there and ended up picking one and going for it.

That's impractical for a number of reasons anyway: Legit GC's have accounts at contractor's-only lumber yards where they pay up to 50% less than you would at the big box stores (on some items, others are 10-30% less, some are about the same price), so even after their markup you're probably still paying less for most materials through them than you would on your own.

The water went through to the basement as well causing damage to the ceiling and walls.