It does seem that rates are going down, and at some point like you say we will end up refinancing to a perhaps somewhat larger rate on a 1st position mortgage to consolidate.  

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 see people owning much larger housing space and paying more for heating, cooling, insurance!!

Larger, more unique do better. 

The single family renovation is financed by a different lender than the larger development parcels.

Staggered balloon payments allows you to plan in advance what years would have the larger gains.

He was attacked by pirates, both he and his dog were shot. 

I’m looking at a similar strategy as you, starting with a small investment first — but I’m eyeing a larger investment in the future for sure. 

With many buildings the larger the unit and the higher the floor the higher the taxes.

If I were you, I would be thinking of doing an opportunistic 1031 exchange of the condo into a larger building.