And if you only talking $1-200k it is not a massive initial reduction depending on their basis.

Depending on who you're targeting to rent your MTR, each website has it's benefits.

Always trade offs, especially depending on how long that buyer is looking to keep the property, or refinance.

A lot of this process depends on your laws regarding STR and Mid term leases/occupancy?

The sky’s the limit, however, depending on the sophistication and the amount of due diligence help you request. 

On an annual basis, the administration is mostly meeting minutes, resolutions, and annual filing of your 990, most of which can be outsourced depending on your budget.

If you are thinking out of state, it really depends.

And this does not include the real world issues, namely are you even allowed to convert this property to a four-unit and taking a single family to 4 unit is very likely going to cost more than $110k (but this depends on the actual layout and work scope).

If they are able to remove the term it will be dependent on the loan underwriting requirements, not because they want to keep you as a banking customer.

If you keep the footprint of the home the same, you can avoid timely and costly site planning applications in most jurisdictions.