If it's a cash deal to keep as a rental, I would approach it totally different than if the intent is to re-sell and the buyer will need a traditional loan. 

I experience this pretty regularly with airport owned hangars, so the rules may be different on a ground lease, but airports tend to be touchy about what's in a hangar and have very clear cut rules about using hangars for airplanes. 

We are trying to move to a different part of town for financial, and personal reasons.

Every market is different but there are things to consider (my first job out of college was bidding on properties at the courthouse steps):1.

Personally, I would like more flexibility in compensation as it often could make up the difference in parties reaching amicable terms.

I definitely wanna learn more about the different neighborhoods in Orlando.

But here I am, trying to put a really strong offer in on a home and I’m not sure if I should go in with the mindset that it’s a 3b/2ba 1,895 sq ft or a 4b/2ba 2,055 sq ft… Seeing as I’m going to rent this one day, if I myself decide to get it assessed/permitted as square footage (which I don’t know how much of a pain it truly is), I ran some rent estimators online (RentCast.io) and the rental comp differences between those two scenarios is about $2,275/monthly vs. $2,600/monthly, which is huge!

Office is a different type of loan.

Next to doing a lot of searches yourself it most likely makes the difference with having good agent contacts. 

@Stephen Montez from what we see here on BP:1) Investors NOT knowing how to get properties under "market" value.They all expect to pay price in MLS and cashflow.2) Not taking the time to understand different property classes and their pros & consThey often buy a Class C rental for the low price, yet expect Class A results.3) Trying to DIY manage without doing their homeworkThey try to penny-pinch, yet their mistakes cost them dollars.