I really hate to micromanage, but I've come to the conclusion that people become control freaks for a reason. This is especially true when it comes to your insurance. I've been dealing with an insurance situation that never should have happened in the first place. Part of it was my fault for not micromanaging an agent and the other part was their fault for not looking out for a client.
Do yourself a favor and put on your cellphone reminders to make sure that all both of the following are done each year.
1. Insurance
2. Property tax
Now if you have a mortgage and you think that your bank takes care of this then your probably right, but not necessarily so. They mess this up all the time. So you need to call each place to make sure that each insurance bill has been paid by them. If you're responsible for it, then don't wait for your agent to do it or call you about it. Trust but verify!
Property tax is easier because they all come due at the same time. In Florida you can first pay it in November and I'd recommend you doing it then because the extra interest each month they charge you isn't worth it. With that said, after a few weeks I'd call the county to make sure that they received the payment. Trust but verify!
As you own more and more homes free and clear this becomes a bigger and bigger issue to keep track of.
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