This is evident when they express their goal as “ I want to own enough real estate to provide me a $10,000 per month income to replace my salary”.  

If you have to replace a roof or HVAC in a few of them you are down tens of thousands of dollars.

And then they come back every two years yes.One of the smartest moves for investors is to replace original windows with vinyl and also make sure the home is vinyl sided.

We replaced everything.

If you are doing major renovations that could change someone's opinion as to the value of the rental, then you should wait until those major renovations are complete.For example, if I were painting and replacing flooring in a couple rooms, then I would advertise now.

For curtain rods, charge him replacement costs; for curtains, go to a thrift store and see if you can find some that work and charge him depreciated value. 

We put in around $30,000 to replace the roof, floors, paint and kitchen.

I can easily replace him as PM on my first property, but how do I get him to give me the lease?

The property already came furnished, but we had to replace most of the furniture because it was very cheaply done, Plus, it had no theme and we really wanted to make it a special themed airbnb.

With a few of our STRs being glamping tents and RV sites, the cost of a policy to cover a the repair/replacement of a tent or picnic table is not worth it in my opinion.