Welcome Chris, make sure you come to the Mid Atlantic Summit in Philly this Spring, an awesome weekend long real estate summit with hundreds of attendees and awesome speakers covering all aspects of RE investing.

I’ll be renting out the upper unit while living in the lower with roommates covering 100% of PITI.

You may have to cover those costs.

Here is two pictures of two streets compared in a multi decade time span as extreme examples,  one of a cash flow only area and one pic of both CF/AP.Which investors do you think had the better and more reliable returns?

I manage vacation rental homes in Charlotte area, and I recommend you have the following:House specific cleaning checklist per home w/condition section for cleaner to fill outHouse specific house info sheetsHouse specific check out checklist per homeIf you get these three documents done well, this will cover the majority of questions that arise from guests and problems with the property that arise before and after they check out.

That means getting it listed on MLS with a competent, full-time Realtor.NAR studies (and there is admittedly a case to be made there for bias) have consistently shown that homes that are sold through a Realtor fetch more than enough additional money to cover Realtor commissions. 

I have funds to cover around 100k purchase, what should be my general road map on the funding?

If there are things of real value, I might look to store it for 30 days (take pictures of EVERYTHING) before finding an alternative way to get rid of the items.

What does landlord insurance cover if you're investing in an apartment building with 100 + units?

Also, what's covered by this insurance.