It’s a competitive market right now but there’s always an opportunity around the corner!

but I also was wondering if some of the well seasoned pro's wanted to step into and give there two cents on Boston, from what I can tell, it's a very rental heavy place because of all of us college kids, but it also seems like its very expensive, so I was just curious how does everyone go about finding deals in such an expensive market?

If homes are selling for $325k and $330k and $317k : I would list for $300k ($295k) If they are selling for : $355k to $370k : list for $349k : etc etc : every market is different and you have to assess the trends, assess your pool of buyers, assess your competition (active listings) and so on… Make a move and reduce the price.

If that were the case, you could simply ask them how they can be so competitive..

Really, it's infinite because you can just add more team members as you get more properties.And I don't worry about competition because at least 80% of STR owners don't know how to market their properties.

Sounds like a great potential solution but also sounds tech heavy and that means when it breaks its you (and probably only you if you are doing the scripting) that can fix it. 

@Christa Parsons I would do research on your competition.

It's competitive, but scalable.

To do a first investment as a short-term rental and win, you have to know the market, understand the HOA structure and allowability in FL, you have to know the management costs (could be 15-20%), and the science behind pricing, changeover/cleaning, and competition in the market.

Do a rental stress test on the property, figure out the maximum mortgage payment you can do, considering a more competitive rental market in the future where rents go down 30% lower as a worth case scenario.