What is the best way to analyze how much ROI I would need to make on the extra cash out to justify paying the higher rate assuming I am going to keep the home for 10-15 years then hopefully trade up with a 1031?  

.- if you plan to put a fence where it’s questionable with trees and crazy neighbors, maybe just talk to them before trying to justify using the existing fence line and see if they would be happy if you would pull it back 1-2’.

Fees should be clearly stated, easy to understand, and justifiable.

A lot of my clients have found great STR deals here, so I think the A rating is probably justified, but I don't spend a ton of time looking at other markets anymore.I picked San Antonio for myself about a year earlier, looking at a number of factors related to real estate investing, but not STRs in particular.

I just don't know.The places we looked at were 1/2 the size of your place and are more of a bargain for visitors rather than an over the top experience like you are planning so I never really looked into that sort of decor.I will say that the prices didn't justify the nightly rate. 60-90 a night just doesn't cut it on a 350k purchase for us.

How do you justify the deal, because if something may happen, big expense or Fed raises rates higher for example, now you are loosing money right? 

Fees should be clearly stated, easy to understand, and justifiable.

I assume that you like SmartBNB's messaging that much better than Tokeet's to justify using a second software just for that?  

So unless more comps with ADU come onto the market, it will really hard to justify the value of ADUs.I hope that help explaining the ADU situation and provide some insight why the value may be low.

In my opinion, I would go ahead and rehab the basement if the comps suggest that adding the additional unit will justify the rehab cost.