A major roadblock to this, however, seems to be health insurance. 

The fact that a lot of small time landlords own the majority of the stock is a problem and an opportunity at the same time - everyone wants to buy one (which drives prices up) and there are some sellers that don't know what they are doing. 

Majority just dnt know where to look to find deals or where to get leads.

This is common, there are usually some justified reasons to get tenants out such as a major remodel or if you plan to live in the unit yourself, however you should have read the rent control rules and had a plan in place before purchasing the property. 

In 20 months since the initial purchase it had a broken water heater a major leak in the front yard watering system, and found that the prior owner severely misinstalled the laminate flooring.

Non-investor locals are having major price shock especially in Northside.I think the bright blue is not working in your favor. +/- $15000 and there are several options within a couple blocks that have more architectural appeal.Apjones is a bit on the edge of the desirable business area for the non-family buyers.The weather this week is going to be very nice... there should be a lot of people out looking.

I would say I use it on a majority of my listings.

Using majority of the $300k, say $250k toward a down payment could buy you a $1m property.

The major 5x4 area South of the impromptu dryer vent hole we pulled out altogether and will re-install new hardwood.

Some part of Austin are great (Galewood area and some parts around Oak Park) while majority of remaining part are very rough.