I'm of course going to ask the owner if the unit is legally a triplex and I did confirm on atlas.phila.gov that it is RM-1, which is good but wanted to see how I can confirm through online records that it indeed has 3 units and not 2.

When your rental income and deductions are on Schedule E you deduct in the year you pay, period.3) Read through the IRS Publication in Rental Income and Expenses make sure you are keeping records and deducting everything you can. https://www.irs.gov/publications/p5274) If you spent 250 hours over the course of the year on matters relating to the properties you can take the QBI safe harbor which deducts 20% from your final after-expenses number.There are other areas to look at in your tax picture that can impact the amount you pay over (your top tax bracket).

I have since then increased my net worth to over 100k invested and completely debt free with a credit score of 745.

If your wife just got her real estate license-how much does she think the home is worth both for renting and selling? 

From a cost perspective, do also keep in mind that it may be worth it to pay a few extra bucks for someone you're looking to build a long-term relationship with if you really think you are a good match with them.

if you're going to be buying a major investment, it's worth it to go there in person.a lot of investors who bought houses sight unseen regretted it later... you want to see the house, be there for the inspection, meet your team, etc.why not 'invest' in that way?

For me here in Chicago, I think it's more risk than it's worth because of the strick landlord laws. 

If you are buying new construction, from a major builder (you know, where they pour foundation on Monday, and framing starts on Tuesday) then I would be concerned.Lead paint, for me, has never been an issue (but worth knowing your locality's policy).  

I’m wondering if it is worth it to send them to collections?

You'll need to be able to substantiate your status if you're ever questioned about it, but it sounds like you're really good at record-keeping already, so that shouldn't be an issue.