My properties are managed by 3rd parties and the accounting software is "baked" into the property management software.I don't know how big your real estate empire is but from my perspective, and as someone who is very skilled in Excel, my recommendation is that you find a good bookkeeper who is really good in Qbooks and have them assist you with setting up your company the right way in Quickbooks such as chart of accounts, categories, lists, etc.

Besides the college rentals, you may want to your shift focus on other areas in town where the rentals are thriving as well. 

I have to admit that after reading your detailed response, my entire thought process and perspective towards and regarding Wholesale Real Estate has been challenged and changed.

But keep in mind this is the perspective of someone who vetted vacation rental property in beach and ski communities and never pulled the trigger.

It looks like you're earning a return on your SFH investment that is greater than the 8.5% you're paying on your student loan, so from a pure return on investment perspective you're better off not paying off the student loan debt.

How would subject to work in a wholesalers perspective, or is this even a possible option for wholesalers?

I'm not a tax professional, but I've talked to several about this, and here's what they've all indicated to me:From an IRS perspective, the amount of time you hold a property is irrelevant.

I guess you could drop your rents if you passed those expenses on to the tenants, but that doesn't sound ideal from a landlord perspective. 

Simply put, from a strictly financial perspective, I'd rather invest my money in something more profitable. 

To give you a different perspective from a different field,  I  have  one yearly membership that is $300 a year and another one that is $500 a year.