If there have been recurring flood claims, then the flood insurance will be higher and you will have issues in the future. 

Now that I have been talking about it constantly with her for 5+ years I know what her priorities are and I try to have conversations that will cause her anxiety by putting our personal home and finances in a place that would feel too risky to her. 

I believe starting it will remove alot of her anxiety but how do I make her comfortable enough to allow me to jump into our way out of the 9 to 5?

I've also been looking for a great contractor, and had lots of anxiety around finding a good one.

If you can rent it and pay your debt service and recurring costs then yes.

Remember, this is an investment and you'll constantly be making sacrifices in order to keep the tenants content.Of course if it starts to become a recurring issue, I would keep record of the amount of time you personally invest in the remedying of these instances and charge accordingly based on recorded fact (write it down, take pictures, receipts, etc).

Hello all,     I wonder if there is a group local to the extreme SW suburbs that has a recurring meetup? 

I originally chose this arrangement as my dog has separation anxiety.

Focus on the recurring themes that indicate a bigger issue (e.g. water leaks in 1/3 of the units).

There is also a strong argument for “it depends” on the type of rental properties you own and what your current time commitments are.example: SFR should result in a “greater sense of ownership” from your tenant and fewer minor/recurring maintenance calls (in general), so being your own prop mgr should require less “day to day” time if you properly screen your tenants.For a different example: multi-family will have many more small maintenance calls that you (or your prop mgr) are required to address, so being your own prop mgr will take a lot more time.And most should agree, if you get a prop mgr, make sure he/she is a good one or you’ll lose money and won’t achieve any goals as a REI.