This isn't like business contract negotiations that recur every so often with the same players.My perspective is that you need to ensure you're reputation in the area is maintained, but not that any particular seller feels that they are winning. 

If you're looking to tap into the capital in your house and use it for a down payment on another property, then refinancing at a higher rate could potentially make sense if you count the delta between your current and increased mortgage payment as a recurring cost on your new property and it still cash flows. 

-Get a non-FHA mortgage, pay the recurring PMI at first- knowing it will (hopefully) go away after I've built up 20-22%+ equity in the property.Assuming consistent PMI costs and interest rates between options (before &/ after refi), the only scenario in which I can see the second option being more beneficial is if I had put enough money down to hit that 20-22% equity level within the first 12 months.This seems implausible due to mortgage payments barely paying off any principle in the first year, not to mention I'd think the only way I could attain that level of equity so quickly is if I had put down 15%-18% initially, which virtually eliminates the benefits of a "low" down payment.I don't have any specific properties, institutions, or rates in mind, and while I'm sure these questions would be more easily answered on a case-by-case basis, what are some considerations I may be overlooking?

Also it allows you to set up automatic, recurring payments.

Also if that is your tenant I would make sure you use a management software that allows you to pay rent online so the parents can go in and setup recurring payments on their own instead of the parent writing a check to you or them writing a check to their child who writes a check to you.

Some buyers will not purchase a property that has evidence of a major repair out of concern that the repair was not completed properly or that it may recur.

By the time you get the invoice, sort out if it is recurring or not and give notice to the tenant, there is quite a lag.

I currently have set-up a recurring subscription with my real estate agent.

A general rule of thumb you can use is: Repairs + Maintenance Expenses include all the costs that tend to be recurring and keep the property in the same condition.

Banks need to give loans and commercial loans are held in house typically so that is their main recurring revenue source.