Till then, .. till I am so friggin filthy rich I will call good people, "the help" and I can afford for a few little people to massage all my extremities at the same time  and I do mean all extremities (eeeewww) I will continue to hustle my butt off till I am seriously DONE!

Are there ways to gently convince the lender this property is more residential than it really is?

You can let them know in a gentle and non-alarming way.

I would try as gently as possible to walk the manager through the missing funds and try to reconcile those, then part ways as soon as possible.I would also HIGHLY recommend changing the way you operate with regards to taxes and insurance payments. 

Both tenants have 5-yr extensions and one has very favorable rates (nearly 50% below market NNN rates and is on gross terms).Secondly, is there anything to do to help massage the very cheap psf tenant closer to market and/or to get them to NN or NNN despite them having an extension option (don't have leases yet so unclear what terms are in there)?

Have a contract on a 10,000 sq ft (main floor) commercial office building with a mix of tenants such as dentists, massage therapists, insurance agent, and real estate company.

The first one in mind is a reasonably priced SFH zoned commercial with room for the front half to become work area for her massage therapy clients.

I try to gently let tenants know that each fall/winter, in an really old graystone, there are probably going to be some occasional incursions.

I would be gentle at first and remind him how long it has taken and Your willing to be easier to communicate with and make quicker decisions!

But I saw today that a good portion of this number is people seeking second (or even third) jobs just to get by.Numbers can be massaged any which way.....we must stay focused on reality.....