Customers in the shoulder season appear to be much much more price sensitive and highly prefer payment plans.

Past renovations I dealt with one single contractor who managed the project but this projects appears I might have to go with a plumbing, hvac, and and additional contractor.  

So, appears to be you going down a rabbit hole and puffing your chest out to show how smart you are.Can we be done now?

Of course it’s not as simple as it appears.....lots of hidden costs, taxes, insurance, preservation, etc. and much depends on the jurisdiction as to length of foreclosure process. 

On the other hand, my most recent apartment purchase was from a large, well-established REIT that appears healthy, and I have not been very impressed by how they ran their business.

Every system you try will have flaws, or you may salivate over a feature that appears in other software.

"Normal" if anything, but at a whole different world of pricing it appears. 

The ones I have heard of/tested are as follows:Beyond Pricing, PriceLabs - are automated pricing toolsLodgify - is strong in website development (if you want to drive direct bookings) but from what I viewed are not as strong in the management toolsYourPorter - Cleaner communication toolOneRoofTop - decent tool set, heavy lifting, questionable sustainabilityMyVR - expensive but decent tool setBookerville - their customers love them, their technology appears to be old school (so does their name)I too am on the hunt for a solution because I want to become more passive, moving away from the daily grind of working "in" my business so I can work "on" my business. 

.- I have the skill set to do majority of the work - the numbers appear do work well as a STR- the property has sat on the market for a long time (100+ days)- I am assuming material and substrates will cost significantly more then doing the same work in the lower 50 states.- the topics I search on BP appear to all be pre/mid covid, and have some recovery discussions post Irma.

First - Have a conversation with your CPA to see if will be beneficial. it appears that you are unsure based on the phrase "hoping it would benefit us".