I'm in the process of setting up an LLC and my wife will likely be setting up an entity for a non-REI business shortly.

People who are looking to buy are looking to set down roots, maybe have a family - in short, they're probably looking to stay a while and will want to have a lot of bases covered right off the bat (whereas renters may be thinking they will move or buy elsewhere 'when the time comes' whatever the 'time' might be).

I recently bought a condo at Madeira Beach for vacation use and short term rental, but I'm not very pleased with the company that is managing it for me. 

A B class property in a C class market will not attract B class tenants or rents.

Deals come up all the time where I'm from, via Foreclosures, Short Sales, etc. via Properties selling for $50,00 - $60,000 .If I get n accurate Estimate that the ARV will be say $80,000 - $85,000 , and Im All-In the property for $65,000 ..... then would it make sense to do the deal ?

The building is going to attract the tenant and if that tenant doesn't allow for systems to be in place and steady passive cash flow, then you might want to pass on this deal. 

If you are trying to do both cash flow and appreciation then you may want to sell it in the next 5-10 years and realize your increase in value and this would be more difficult in a "run down" property and it may not appreciate as much anyway.Another thing to keep in mind is that a more "run down" property will attract a less quality tenant which can create more stress and worry.

Sure prices go up and down over time, but not to the levels we saw in the short time frame we saw.Peter Lynch once said that more money has been lost by people trying to anticipate market corrections than has actually been lost in market corrections.

My short term goal is to try to master wholesaling and then move into cash flow properties.

This attracts a lot of out of state investors who think that the low barrier to entry and high tenant pool equates to high cash flow at double digit rates as it would appear on paper.