Bad contractors are one of the main reasons why first time investors never do a second deal.

Quote from @Tove Fox: I live in California and am interested in purchasing my first investment property in an A or B neighborhood in one of the above states, ideally under $300k.

Did anyone in one of the accounts die?

You and Him are filing one joint tax return. 

Here is one piece of advice When looking at areas to invest in check out this website https://www.areavibes.com/ its pretty cool it gives you a total livability score and rating for that areaBest of luck!

As our team has grown, it's become easier to cover responsibilities if someone quits, goes on vacation, or if we terminate employment, compared to when we had one or two homes. 

My goal is to buy one rental per year with price between 150k-250k for the next ten years (if i get to keep my job). 

Quote from @Robert Zajac: 15% markup on maintenance is one of the highest I've heard of.

I'm having a hard time believing that as I've never seen one installed like this. 

Or should I find a property first and hope that no one will get that property under contract right away?