It’s an amazing location, double block with albeit a beautiful run down house that looks like they may have encountered financial problems/heritage permit problems.I’m  thinking about dropping a letter in the mail box with a super low ball offer that will hopefully give me an idea of the owner ever swings past or not.Love to hear if anyone has had any success 

So my work in the family business wouldn't support me getting my first mortgage - at least not from that lender.Will I encounter the same problem from other lenders? 

You're also less likely to encounter ungrounded electrical systems.

What problems did you encounter and how did you overcome or work around? 

This is a great site for knowledge and no matter what you encounter most likely someone here has experience in it.

If it were mine, Loud boy one warning--then non-renew--or boot out.Car issue, number the spots and assign them in the leases with a parking sticker with the spot number on it.Staple a duplicate numbered parking sticker to the lease in case you ever need it in court--vs peeling the one of the renters car.Possibly do an addendum for this to the lease if need be.Post warning signs according to local law and set up with a towing service.Car issue with no sticker parking there, have resident have service tow it--according to local law.No need to get involved in the car issue then. 

@Jessielyn Laroa just keep refreshing your browser or close it and type again if you encounter that..

I was wondering who might be brave enough to share any unexpected pitfalls/struggles that they encountered by being their own property manager of a multi unit apartment.As I began thinking about managing a multi-unit (especially one such as a 10-30 unit dwelling), I tried to think outside the box about possible unforeseen challenges outside of the typical calls "my sink doesn't work" or "my toilet doesn't flush". 

Any roadblocks to look out for that others have encountered with development in the state?

Scott's book will provide a helpful start in teaching you the categories of fixes you may encounter and their relative (but not absolute) prices in your particular market - and having the contacts necessary to put your plan into effect in a timely way.