@Jase Machado I'd have a tough time giving up a 2.75% interest rate on the primary loan.

When I walked out of that office, people had smirks on their faces expecting me to be back in Corporate America within 3 months because ya know, "it's tough out there, 90% of startups fail, real estate is risky and the list goes on".

Tough to do, but you both will benefit from having a candid discussion so you can calibrate each others professional expectations to arrive at a mutually beneficial conclusion going forward. 

Some general contractors do certain trade work in house and other smaller guys sub out a lot of things to keep their overhead tight, because they don’t have to carry workers when they don’t have work.

If you're logic is that you feel like you'd enjoy paying 15% less, it's unlikely that the seller is going to want to sell.However, if you come to the seller with some information about why you think you're asking price is more appropriate (rent is lower, CapEx or repairs needed, etc.) you will at least have an opportunity to talk about it, without frosting the seller.Extra bonus note: using the fact that it's been listed before or been on the market for a long time as justification for a lower-than-asking offer on one of the lowest cost assets currently available in your market will DEFINITELY frost the seller.You'll need to get your hands on a rent roll or a pro forma, too ... it'll be tough to do good analysis without the basic numbers, even if they are padded a little.

Think of a duplex, where you can live in half, and rent the other half out...you are in the learning mode now, it will be tough when you need to get on a jet every time to check out the house, and helpers. 

@Matt Ashbrook I’m in the Tampa Bay Area as well and it is freaking tough to find a multi.

These are tough situations to deal with. 

Again its tough, because I am self employed, and make very little in taxable income. 

Someone needs to oversee the finances and legal and someone needs to oversee selections and managing the workers.