If you believe that what you are proposing is solid, your confidence will help sell it.  

Thanks to David Greene I feel more confident doing it

It was just what I needed to finally get serious about my real estate investing and now I have the confidence to say that I will complete my first real estate deal in 90 days. 

I feel confident that he did not do a back ground check on my tenants.

But, as you point out, it eventually will be in that 5th year, if your prediction holds true.So, if I were confident that $15K is the correct repair cost, and also that 5 years was the likely time-frame, then I would wisely set aside that $3K each year as an actual expense that would come out of income and go into a separate CAPEX account for accounting purposes.I would then adjust my NOI number accordingly and recalculate CoC.

He is, however, confident that he could get a renter at that price (though there may be a $50 discount incentive for a yearly lease which I would prefer due to less damage moving in and out).

Most importantly you need to convey confidence and assurance you are a player and not just wasting their time.

Without gaining a certain level of confidence, it will be tough for potential investors to get comfortable enough to invest.  

Then you can slowly build up a network of vendors on small jobs,And gain confidence in managing larger jobs.You will also get an idea of how much plumbing clogs, painting, changing locks, taxes, and all the other expenses that come along with RE cost.

There is value to peace of mindI am willing to invest out-of-state -- in fact my research is suggesting I might have toI want my portfolio holdings to grow in door numbers as I mature as an investerI LOVE the concept of BRRRR to keep that capital available and working to expand a portfolio, but am not confident that's the best place to start outThx - Dan