-We want to build something small, and unique.

@James Cash your scenario isn't unique to just fourplexes, rather, it's all FHA Home Loans for owner occupants.

@Jordan Lucas My experience has been awesome, First  I  affiliated myself with a RE Real estate investment firm (they wholesale ) now the cool thing is that the company I work with have a unique system that allows us to have constant flow of deal and also a great CRM for our investors (quality investors) So I saw that on that company and then decide to leverage from that, Make money and use it as University (basically )  I'm still learning and you never stop learning.

If he gets out of rehab and wants to work on a repayment plan, great.... but you don’t want to be 3 months down the road in the same situation.

I believe college offers many unique experiences, -- networking opportunitites and (hopefully) educational enlightenment and if you don't take advantage of them now....it might be tougher (although doable) to get back to them later in life. 

I like the idea of selling a unique place for short term rental.

Yes, each deal is different and no loan file is the same, therefore each DD is unique.

You probably have to go into neighboring towns that you can make an argument for being similar in demographic and proximity to transportation, or whatever makes your property unique to justify your price.

So I have been looking for a Real Estate Software that would work with my unique business structure.

Maybe my experience is unique, but it doesn't seem that way.