It sounds like you’ve got a solid agent on your hands, and it’s awesome that you trust him.

On the other hand, there’s a part of me that wants to just keep slow and steady without leveraging more debt and buy properties as I can save a 20% down payments.

Investing remotely is totally doable—you just need a solid team on the ground.

You just got handed $300k tax free.

There is more time invested but totally worth it for the increased cash flowHi - what bank did you get your lending from? 

Could be something that could really benefit other investors to understand better from a first hand perspective.   

I reside in Hattiesburg and I recently invested 5K on a Wholesale Program, thinking it would be really hands on and structured more like a mentor program.

I have a property management group in Hawaii that offers both STR and MTR services, but we don't mix for the reason that he mentioned - a single STR booking on an island can totally kill any ability to run MTR.

There is a lengthy discussion comparing and contrasting the "broker" and "finder" parties and their role in the transaction in the court case described here: http://law.justia.com/cases/new-york/other-courts/2010/2010-20104.htmlWhile I realize this does not apply directly to the topic at hand (Wisconsin), I and other BP members in other states should find it very informative and educational.

As a Broker myself in California I woulld say hands down a 7 day listing for an exchange of a buyer is in your favor.