Any company insuring your properties without an inspection most likely has a clause buried deep in their policy allowing them to deny claims for conditions found on the property that do not meet their UW standards and they will deny you claim based on "the house should have not been insured with them anyway".Although the inspections can be annoying look at it from the other side.You pay them 1000 to 3000 a year to insure a rental property where they agree to pay out possibly hundreds of thousands of dollars if it burns down or up to 1 million if a tenant slips on a bananna peel and falls down the steps or the tenants dog bites someone and since you didn't enforce the tenant having their own renters policy to cover the dog bite the landlord's policy is paying out.The insurance company is very much like your rich uncle backing your business venture - you run the business, he takes on the financial risk from disasters, and doesn't even get a say in who lives in the property.Your rich uncle asking you to fix the steps, put up a handrail, etc which is in your and his best interest long term.Do you really want to rent out a property with a busted front step and a bad roof that is going to leak sooner than later?

I'm moving to Tampa and would like to house hack a multifamily.

Frankly, I am hoping for continued cooling but I don't think it will go down a ton but we will see in the next couple of months. 

Be VERY careful, most of FL is correcting and will continue.

The cash flow houses help me to hold on for the long haul, while the appreciation houses enable me to buy more houses.  

Cleveland offers a mix of affordable housing options and a solid rental market.

Tahoe continues to grow as a tourist destination and the low taxes, landlord friendly make it an ideal investment area.

I am currently in the homebuying process, looking to close on the house in the next few months and house hack it.

Part of what I do in developing Workforce Housing How did you find this deal and how did you negotiate it?

Your first purchase with your brother should be a house hack of a multi.