But regardless, I'm in a terrific spot now with the rental, I enjoy being a landlord, and we will continue to hold it forever.

I host the meetup in Orland Park-we were meeting at Champs but they closed, so I will have a new spot for October.

I wanted to select not only a good tenant, but one that also banked/paid bills electronically.  

Of course having a second person rent is never a great situation, that person should have just given a 60 day notice and moved out the tenant, if she could not find another tenant to share the spot with, write the contract for shared rental. 

You triggered a "Hot Spot" with me you rascal you!

The original electrical would have been installed to run a few incandescent bulbs, a radio or two and perhaps an early appliance and was not designed to handle today's electronic demands.Another thing to keep in-mind, depending on when the property was converted to apartments, is that the conversion may not - quite likely will not - meet current fire codes, which will both impact your insurance rates and your renovation costs when you do undertake a substantial rehab.That gorgeous exterior, with it's clapboard/shakes (or era brickwork) and elaborate trim will be high maintenance - that does not mean it's not "worth it", just that you need to budget accordingly.Personally, I enjoy performing deep energy retrofits on these old buildings (which can be very solidly built), but it can be an involved and costly experience, hence we are always looking for the unloved and run-down which can be purchased cheaply.If that house has been 200+ days on market - and no other landlord or investor has touched it - tells me there is a problem with the value proposition of the deal.  

Hi @Chris Matson, Kevin is spot on -  the best thing to keep your operation efficient and running smooth is to get some solid software for managing the business.  

I dont really know the california market to well, but I will be looking for some hot spots real soon or maybe even some surrounding states as well.

Some believe touch up paint means you walk around the house, touching up spots, but that never works as it does not blend in with the rest of the wall, so the entire wall has to be repainted.  

Learn to spot a deal (compared to other properties being sold).