Question is, if I have the means to put a high enough down payment on a house to be cash flow positive (assuming my expense estimates are accurate, etc.) is that something that I should do?  

This indicates a strong market for short-term rentals.Revenue: The average revenue per available rental in Red River Gorge can be estimated using tools like AirDNA.

These softwares have a lot of functionality, but honestly there is a steep learning curve and the functionality is probably overkill for most rehabbers.FlipperForce - Web-based House Flipping Software built specifically for flipping & rehabbing houses w/ Estimating, Gantt Scheduling, Task Management & Budget ManagementGeneric Project Management SoftwaresThere are nearly an infinite amount of potential generic Project Management softwares available that provide powerful functionality for managing project schedules, tasks & documents. 

I attached rough estimate on here, I included rehab on to the sales price 

Quote from @Roger Garner:Multiple estimates and get some photos of their work too.

.: I would personally ask for a price decrease based on whatever estimate they got for the installation of that equipment (assuming you can get a loan without those things - depends big time on the bank - my local banks would do it for me). 

Property is fine as is but if fully renovated in my market I estimate 500k-550k ARV.

If your ARV is truly $285k, then I would estimate you could cash out around $135k that you could apply to the DP of the 6-plex.

I need credibility, either through working for a couple of years for a company or buying my own property, starting small, and scaling with time.Now, my plan is to graduate next year (Im a junior), and get a job in a firm as an analyst in order to build that experience and mainly cover my living expenses, while on the side buy my first small property and go from there.However, and this is where I start overthinking,  I still have 1 year left in school and I want to use it to my advantage as I don't have any expenses or responsibilities other than school yet, and I want to do my first deal.

If it was just my house sitting I would say I over estimated the sales price or over rehabbed, something, but it is most homes in the same area that had been moving so quickly are now sitting for months and are all priced according to market value.