I have been generating a "short list" of different markets of interest, and one of the areas that seems promising for short term rentals is Branson, MO.

Seems like there's a big range depending on who you ask. 

I own my own business/LLC and am open to changing that structure for tax purposes, such as putting it under an S- or C-Corp if it would help with this situation.)I appreciate any and all thoughts on this matter as I can't seem to get out of my own head on this!

Seems like it could be something to do that could make the cashflow work more.Reason I ask is as I put proformas to see if buying a rental is better than investing in the market if I had the same cash available to start and additional cash flow each month (or negative)Thanks

It seems like the others are telling you to take the practical approach to the situation and you are going to be better off exerting the energy and money in new opportunities.

If the numbers are checking out, the foundation still seems sound, electrical, and plumbing has hopefully been updated, roof, gutter mechanicals all looking pretty solid, you are doing fairly well.I also take the stance that, if a property has been there over a 100 years and is still standing, you know you have a solid house.  

Look into statute of limitations when it comes to utilities - which seems to (sometimes) follow contract law.

I'm looking to buy my first apartment in Johannesburg as yields seem to be much more attractive there.

Then again, every time we resolve to downsize we seem to grab yet another opportunity.

Usually those apartments get rented in days and homes under contract in a week or less is what it seems like...as long as they are priced right.