If you're logic is that you feel like you'd enjoy paying 15% less, it's unlikely that the seller is going to want to sell.However, if you come to the seller with some information about why you think you're asking price is more appropriate (rent is lower, CapEx or repairs needed, etc.) you will at least have an opportunity to talk about it, without frosting the seller.Extra bonus note: using the fact that it's been listed before or been on the market for a long time as justification for a lower-than-asking offer on one of the lowest cost assets currently available in your market will DEFINITELY frost the seller.You'll need to get your hands on a rent roll or a pro forma, too ... it'll be tough to do good analysis without the basic numbers, even if they are padded a little.

Love the enthusiasm.I'm from Indianapolis as well and would enjoy connecting. 

While I’m somewhat familiar with real estate (from purchasing my property, reading, podcasts) and have enjoyed learning about it prior to this point I know I have much to still learn.Knowing what you know now, what would you recommend to a new residential agent when getting started?

Free up your time to do what you excel at, enjoy doing, and maximizes return.  

I really enjoy my day job, but will want to have more financial freedom before I turn 60.

I enjoy looking at numbers and underwriting deals though so if I can ever be of value that way let me know. 

I think there's more to consider than just money, to include your existing tenants' right to quiet enjoyment.

Right now, im enjoying being a dad and it has actually helped me slow down and take breathers.

All the best in your endeavor.

@Kelsey PyleHere are my go-to's:The Handyman (Enjoyable content, love this guy)The Handyman Business (Enjoyable content, learn about the business side, and hear funny rants)Home RenoVision DIY (Actionable lessons, how-to's)This Old House - of course..