I think your best bet is to get an inspector out there before you buy.

And also If you could plan a trip to coordinate with some of the meetups that would be your best bet. 

I agree with Jaysen, with 200k to invest I would be looking at mid size multi-family properties.

I don't think $20k is that far off if you are hiring a General Contractor to manage the project.If you manage it yourself, I bet you could get it done for somewhere between $10 to 15k.  

If I was buying something that size I would negotiate the price such that I got those numbers. 

As important as it might be to know what a GOOD deal looks like, I would bet dollars to doughnuts that it is just as important to know what a BAD deal looks like. 

As important as it might be to know what a GOOD deal looks like, I would bet dollars to doughnuts that it is just as important to know what a BAD deal looks like. 

Once booked, you can bet they'll be combing over the photos with a fine toothed comb and a gleam in their eye, and sharing the listing with friends and family (or fellow guests) as they envision their actual stay there. 

Have a good sized cash reserve and know you can pay 6 months of mortgage without a tenant  I would say put at least 20% down if possible  

A recent value add that I saw, but this one required capital, consisted of subdividing a lot and rebuilding the original house (with a monster size house) and adding an ADU.