We have been in the attic and there are no signs of water coming through the roof, i.e. there are no water spots or discoloration on the plywood, so I believe that we are talking about just replacing all of the shingles.

the saying goes, "the leopard doesn't change his spots"....so I tend to agree with the board, and my only caveat is that you really want to know will he pay the rent...I have had a few very good long term tenants who made rent a priority but still had the errant medical bill or consumer credit problem..so I would really probe every landlord and the rental history, but recency and amount of payment  issues tends to indicate that if he won't pay others, he probably won't pay you..a vacancy may be better..with an empty unit, remember an ideal tenant could call anytime..you may have to cover the mortgage another month, but you also cover it if he doesn't pay, plus evict, and re-prep the unit....vacancy wins unanimous decision...

All in all though, your post was pretty spot-on.

The sweet spot for cash flow is lower in a market, typically.  

And just as many that specialize in turn key sales .I would not get to focused on one area until you have explored much of the US markets first.things to consider when owning rentals of course is the city health and demographics and long term projections.. and the other big issue especially with older rental stock is long term Capital expenditures to keep said homes in decent shape.. there is a sweet spot for rentals IE sq ft of homes and bed baths..

Good time to be a home builder with 12 under construction and 4 pre sold... sure beats being a seller in 09 and 2010.PDX is uber competitive on the fix and flip side of the coin.. but people do it every day.It finally dawned on me to go for larger deals.. less competition and I can work in the same spot for a few years. 

Millennial buyers are still a bit non-existent due to affordability gap and the tendency to rent, but when they have the money and start buying (5-10years) I think Oak Cliff will be one of the spots.

@Alexander Baez Parroting what Brie said, you're in the right spot.

This is key, but again, if you DIY PM 1st, you'll learn this very quickly and know how to spot it in a PM you hire.

In addition to my real estate income I work at Sleepys (mattress store) which brings me to about $75,000 per year, but because my job is commission based I need to show 2 years of consistent employment in order for the banks to consider my income which leaves me in a tough spot for a loan.