The second DTI ratio looks like it will be my primary hurdle for all future conventional financing unless the rental income starts meaningfully contributing to our regular W2 income.

A next level profit potential, maintenance insurance, for a monthly fee it covers certain regular inspections and portion of costs for minor repairs.

I have done a bunch of reading, inspired by Brandon's article, and can only conclude just about any person who is regularly buying and selling houses and has no other income would be a dealer. 

Unfortunately tenant's do things like this fairly regularly.  

Insurance companies rank them as an aggressive breed and some will not insure your building at all and others at 3 times the regular cost.You can ask the tenant to get their own insurance for the animal but they tend to get insurance for one month and then drop the coverage and never tell the landlord.The dog biting other tenants is a real concern.A young family might be concerned to rent your units but as mentioned another dog lover with a high risk breed might find the situation a plus.  

You can't enter someone else's home unless it meets the conditions of your lease (regular inspections or notice given in xx hours advance to make repairs or let the property). 

We regularly give the three basic options for coverage that you will hear debated on BiggerPockets.  

I was thinking of converting from a regular IRA to a SD Roth IRA but failed to state Roth in my first post.

Our regular guy will paint for $25/hr, but we have had to reach out in tight turn-around situations and have paid $40  (and felt fleeced the entire time).

This is palatable and a deal I do regularly.