I did mention owner financing but other than the big sales tax hit I didn't know quite how to sell that idea to her.

In 2008 this was one of the areas to get hit the hardest.  

You can ask for disclosures and financials and all that from boards and HOA, but at the end of the day there's no guarantee you aren't going to get hit with one. 

Outrageous considering we can re-roof and reside cabins by contractor without hitting a 10k deductible.

It was silly for you to respond but regardless, hit up VRBO support and let them know.

My goal was to have 5 properties at the end of year two, but I think that I will realistically hit that number by the end of this summer. 

Transforming SFHs into multi-units and targeting 2-4 units for value-add potential is a smart way to build your portfolio, especially if your goal is to qualify for larger loans down the line.If you're aiming to hit the 5-unit mark and unlock better financing options, here's something to consider:Leveraging BRRRR Strategy: You’re already thinking about the refi route, which is key.

Lastly, they don't get a hit on their taxes until they receive their money, which is a benefit to the seller that is easily over looked. 

I am starting to believe that I need to learn the tax laws myself since I have lost so much money paying unnecessary taxes because my previous CPA's are not familiar with all laws or they just plug numbers into a software (without strategizing) and then I get hit with huge tax bills that could have been legally avoided. 

Those communities were the worst hit during the foreclosure crisis.