I worry because quite frankly our tenant pool isn't one that adapts super well to change, they aren't that technologically inclined (online / app = payments - lol - some of these folks are depositing cash into our bank accounts on the 5th) and I worry that this change will disrupt, cause move-outs, more fees, etc...Thanks in advance for your insight, heckles and advice.

I have been reading on the subject matter and failed to see this point.

Here in Chicago you can't make any fees part of the rent, so no matter how long they take to pay it, as long as they pay rent, they are current.Ideally I'd like to add fees to rent, so when they pay only the rent, it's considered late, and you can add more fees.

Chad, before I start, when I see someone making a loan at 12% interest, it sounds to me they planned to sell the loan at par or very little discount to someone in the industry... big mistake, because industry folks buy at discounts, no matter what the interest rate (at least I do).Anyhow, here's a quick guideline for you when selling notes: How do I plan to sell this loan?

It doesn't really matter if you can't take care of the "minor" issues before they move in. 

Very specific situation I've got here that I haven't been able to find good information online that fits this unique criteria.I have a friend that has a property that they own free and clear of mortgage, yet they are paying a HELOC of approx. $300 a month for.

Motivation is a personal matter in every transaction.

Property this close to the city is limited.Using an online calculator I found and assuming the property appreciates 3% per year and the after tax return on reinvestment if I sell is 5%, I’d still make $120k after 20 years if I rent.

My experience- I tried to do it on my own, online, and researched a lot.

I want to have more saved for just in case expenses for life/a potential rental property but also want real time experience and I think this would be a great way to do it.Your absolutely right that real "pounding the pavement" experience is the best way to gain knowledge and I think it is a reasonable request which someone can say yes or no..however I dont think contacting random people who are investors on LinkedIn or online is the correct way to do it.