But, the question I am now asking myself is, when is it actually a good time for me to begin with my first deal?

If it were written better for them, that would be a deal killer for me. i would negotiate it out.

I’d really appreciate it if anyone has any advice for me on what to try, or to just sell!

I would like to know offer example such as offer to pay full 15% of commission, but lower rent or offer asking rent price with lower commission (such as 10%).Just a quick math, if I paid 12.5% in fee and $1650, then the equivalent rent would be $1856.25 = ($1650 x 12 + $2475)/12Another example would be, 15% in fee and $1550 is $1705 = ($1550 x 12 + $1860)/1210% in fee and $1750 in rent is $1925 = $1750 x 12 + $2100)/12 (this would be higher than the current offer...)So I guess the math says, lowering the rent will help over all cost for me...?

I would like to get a mortgage or some form of a loan for this house in order to "get back" the cash I paid upfront and use it for the renovations (it will most likely be a flip). 

The way that works for me is walking through the house with potential renters and letting them know the condition of the house and what I believe they should call me about.

It gets the point across so that’s okay.To your original question for me if you were pitching me to be an investor with you, the two main things that would convince me is your knowledge of the numbers and costs and you putting your own money into the deal.

So I started looking into real estate investing, the fact that the terminology was easy for me to grab is what drew me in.

I usually just read but I feel it's time for me to reach out,  I currently run an Amazon business full time and while it is successful it still feels like a glorified high paying job.   

These are little victories but both 'firsts' for me and are building my confidence that I can do this real estate thing as my only gig before too long.