I have used a professional tenant before to do work - I have a plumber in one of my rentals, and I will throw him some side work on occasion on other properties - but he bills me out like any other professional would and I pay him separately.

On a rare occasion we will get cash and give the tenant a receipt

In such a case I would look professional but I would not overdress for the occasion.

Then I get a call with someone wanting a bridge loan to close in 5 days since they had to walk away from another lender due to something like this... happens far more than I'd like to admit.And yes, I have gotten them closed in 5 days on a few occasions. 

You have less in the deal and more in reserves for any occasion (yay hurricane season!)

I definitely can get trapped in the analysis paralysis vortex on occasion.

I have had land me the deal in the current market in more than one occasion! 

My current tenants seem financially stable, but in the past I've had tenants whose rent payments bounced on occasion. 

It's all appreciated.Jason, as a fellow REBNY Member, we have access to their Legal department and I have met REBNY's Legal team on several occasions.

I've been referred to BiggerPockets on three separate occasions by 3 completely different sources so I thought I should check out what is going on here.