Well, we quickly realized that our cash flow for the first 18 month would go entirely just to repair the current issues, let alone things that would come up later.Luckily, I can easily commute to Milwaukee and NW Indiana and do my own due diligence.  

Maybe other areas too that are commutable to oracle (if you go into peninsula.)  

Podcasts are my main method of listening to new music, the news, educational/informational stuff, and makes my 1.5-2 hour daily commute feel a bit more worthwhile.When I was in high school, my stepmom (then Real Estate Agent) was doing a lot of BPOs (Broker Price Opinions), and I helped her out by driving around Southern California taking pictures of properties, then bringing them home to her.

@Michael Stroup It sounds like this particular contractor knew you were a long distance landlord and in a time sensitive spot given the AC was for an elderly couple & might have taken a little advantage of that with the price they charged.All you can do now is learn for the next time I guess and take note of this contractor to never use them again.In the end if the tenants pay on time and only call when legit problems arise you will do fine in the long run.

@Brandon Turner my only issue with the podcasts is that my commute is too short to get through more than one per day!

This is why I ask before before commuting to something I don't know anything about.

This alone I can see in my daily commute in just recent years.All that aside, you are spot on...

So here is what I would do if I were you (and I am both a long distance LL and a tenant so I can sympathize with both sides here).First it's good you are venting here and hopefully not to your LL, whatever you do all your communication with the LL/PM needs to be in writing/email so you can document exactly what actions were taken.

Too often, even on this site, I see ROIs that were reversed engineered, meaning they started with the ROI they thought long-distance investors wanted to see, then backed out enough on the expense side of the ledger until they had boosted the ROI into the magic range.

That particular area is a historic district bedroom community where a good portion of the residents commute to NYC.