I have strengths in data analysis and having a full-time job, so I'm hoping those things will make my entry into RE easier :)

Pros are that it's an inexpensive entry point to the south city rental market.

By using lock box files (or integration with Paylease) with Buildium all that manual data entry is eliminated.  

She called and told me when she got home the front entry glass pane was broken.

On the other hand I have a lot of friends that are engineers and their entry into investing was much easier because they had a W2 job and their path was smoother. 

Do you know this (i'm holding my tongue) "appraiser" comes out for the 3rd time and tells us that we now have to repair the whole patio which is near the bilco door and walkway and replace the front entry stairs. 

Banks are players in this space, but you may be getting beyond the scope of your local community banks, so you'd want to start to compare some national bank lender options - some lend balance-sheet, and others securitize (CMBS).I write about and help people through this sort of thing so check out a couple of my BP blog entries here, but please reach out directly if you have more questions or would like advice on how to start up the above.

Here's the short version:June 2011 Purchase by Jane DoeOctober 2013 HOA gets a lien filed March 2014 Judgment rendered to SherriffJune 2014 sold at auction for nominal amount to "Name of street" TrustJune 2014 Forcible entry and detainer citationJuly 2014 Notice of bankruptcyAugust 2016 Eviction hearingSept 2016 Default judgment for plaintiffOctober 2016 Writ of possession unservedFebruary 2017 ch 13 dismissed for failure to make paymentsJane Doe filed ch 13 in 1998 and 2014.

@Michele FischerThis is my lease Clause for landlord entry: Clause 14 Right of Entry-Landlord will have the right to enter the premises at reasonable times by use of key or by force if necessary, to inspect same and to make repairs required therein or elsewhere in Landlord’s property, to enforce any provision or condition of this agreement, and to show property to prospective Tenant or others, by appointment or by use of key.

The bar to entry is 3.5% down that can come as a gift and the seller can contribute 3% toward your closing costs.