SFDC will handle duplicates a bit better than Podio, but it won't really address the other negatives you listed, plus it costs me $5/mo (but I find it to be very worthwhile).

But I doubt I could buy any of them at a price that would make them worthwhile.

You would have to have a lot of rentals to make it worthwhile."

I mean to make something like this worthwhile?

The sales rep acted like I was being unreasonable for thinking it was worthwhile to spend a $200 plane ticket to see a market's active homes. 

If you want to get our opinions of whether a project is worthwhile/feasible, it would help to include a lot more detail, including the numbers...

Is it worth while to pay this extra cash onto the mortgage principal to payoff the debt off quickly?

Closing costs on commercial loans to an LLC are not insignificant, re-fi appraisals are always a risk and at this point it hasn't seemed likely to be a big enough benefit to make it worth while.

It might be worthwhile to see if your aunt or someone there locally can help you make connections to find out more about what is being considered before you make a big investment in getting it running.

Today, it is rare for something worthwhile/priced right to sit long -- however, it would be wrong to assume anything.