In the past couple weeks I began the process of doing a cash out refi with a local bank to pay off an owner finance note I have on the property and to put an additional $30-40k in landscaping, a barn, and a few other items like front porch decking.

Currently, we are converting a barn into an ADU and JADU.

It's apples and oranges to comment from the institutional lending perspective on guys that just want to invest their personal funds and make paper.

I liked the quick multiple quoting process and the detailed question the app asked so you get some apples to apples pricing.I would caution that a few vendors "quote" an on-call visit that they will waive if they get the job so it may appear they only cost $50 or $90 for a $300 job.  

That is like comparing apples to oranges.

In the short term rental business there seems to be a wide range of different types of rentals that are apples to oranges, especially from a financial perspective.

Sometimes appraisers, especially if they are not familiar with the specific neighborhoods, or, if they are from out of town, unknowingly compare apples to brussel sprouts.Anyone active in Fountain Square, Fletcher Place, Holy Cross, Bates Hendricks, Herron Morton or other hot neighborhoods experienced this?

Pick the right set of securities (like my friend who basiclaly just bought apple for the past 20 years) or the right real properties, you can make out like a bandit.Apples to apple comparisons are difficult. 

You need to compare apples to apples, or at least KNOW that you are comparing apples with grapefruits.

It is imperative that you approach the situation prepared and as Alan said, ask the same questions so you may compare apples to apples.To answer the last part of your question, PML's will usually only lend based on YOU.