Having said that I have never heard of a short term rental in a hot area making less on the short term rental market vs. long term, even with seasonal swings. 

You have to value your time - if you have the time to fix them up, then the deal is solid...if you don't have time to swing a hammer, slop some paint on, or replace a toilet, then you're better off going retail.One frustrating thing is there are many folks these days that are buying some of these run down homes  then attempting to rent them out or seller finance them on the condition that you make the repairs. 

Thus, I need someone competent to do a thorough financial analysis to help me understand where the swing points are in the tradeoff where one option would make more sense vs. the other one.Something along the lines of:https://www.nytimes.com/interactive/2014/upshot/bu...but which also incorporated my current investment property holdings.

You've been out of the business for a little while, so take your time getting back into the swing of things before you start becoming personally responsible for more debt in the form of owner finance, subject-to, etc. 

I picked one up and walked through the house, with the 2x4 ready to swing. 

I am a golf professional so I typically snowbird for work.  

I went from owing $14,000 in one year to $6,000 back ($20K swing) in the next year just because I got into real estate and it gets better every year!

Have a couple of properties in a ash flow market can be detrimental as the swings are drastic. 

The question is where are we going to invest to 1) Not lose Money when the shift happens in full swing and 2) How to take advantage of that shift before it's too late?

- You can miss out on a lot of opportunity if you are always swinging for the fences trying to get that home run of a deal.