I'm a member of GaREIA, they have a google group where experienced local inveztors trade tested (and mostly reliable) contractors, legal helps, strategy.   

This past summer was our first year, so to test the market we had a 3 day minimum, and we filled every weekend with 3-5 day stays easily but we had holes in the midweek.  

Buy a few leads—start with a small test amount—and assess their quality for yourself.

Once you have a shortlist, sign up for an account with each one and test them extensively to see how they function.

I also leverage a tool called Intellihost which helps with pricing strategy and conduct A/B Testing with listing changes.The listing description seems to be just a paragraph.

I did a search on vacant properties and then did a drive-by test yesterday.

That will completely break my self-sufficiency test. 

This year we had a heat pump cleaning, testing refrigerant charge (didn't need any added) and a capacitor replacement, bill was $157.05, factor I consider are the age of the existing unit, if it needed a charge, potential leak, cost of refrigerant (over the years there have been many varients of the type of refrigerant). 

If the goal is still the goal and you are willing to do anything to achieve it, then test everything, don't set a path in stone that you cannot come from out of. 

A couple of thoughts specific to condo investing:1) Be sure to include the condo fees into your cashflow analysis, and budget for potential assessments as projected capital expenses2) Make sure the condo association is solvent - a good litmus test is whether or not the units are approved for FHA financing3) Make sure the condo association rules/regs allow for rentalsGood luck!