We will definitely eventually engage a professional, but I wanted to check with you knowledgable folks first to make sure I have a solid strategy going into that discussion.The house was bought >10 years ago for 800k and is now worth between 2-3.3m per Redfin and Zillow.

Even if you engage a broker, you should still shop around an additional couple lenders yourself (if you have the time/energy).Freddie SBL loans cap at 50 units, so you won't be able to take advantage of that program (unless they can somehow make an exception), but there are still great Agency (Fannie/Freddie) programs that would work. 

I probably shouldn't engage but this really wasn't the type of response I expected from this group.

this is a nearly full gut, floors stay, everything else goes. moving walls, new mechanicals, etc. also I guess I know now to draw up rehab plans before engaging contractors.

If you engage with the zoning department on your own you might want to be a bit vague so that you don't pin yourself into a corner.

Since then I got engaged, moved in with my fiancee, and looking for that next deal to keep on with my buy-and-hold goals.Thank you all for contributing as much as you do!

Generally, I think they take better care of my property because they know I own it and am engaged about managing the relationship. 

that's where you want to go hunting.I'm not a lawyer, but a financially sophisticated woman will understand that an engagement ring worth less than $14,000 probably avoids any question over whether the ring is subject to the gift tax.

Gaining first-hand experience alongside more seasoned investors/flippers is certainly a great way to learn! 

Our goal is to be financially free within 3 - 5 years, allowing us to work on this endeavor full time.I want to thank everyone who has contributed to the site as it has been an amazing help and I look forward to staying engaged on the forums to pay that back as best I can starting with this way too past due introduction.My wife and I are focusing on buy and hold rentals and flips in the Chicagoland / Central Illinois areas.