@Matt P. 2500$ a month is what I need to cover my bills so I can keep focusing my time on investing and not have to work another job I don't enjoy.

Which simply means I'm looking for anywhere from -$3-5k to +$3-5k cash flow each year and the ability to enjoy the property up to 14 days per year with family (excluding "maintenance" trips).  

We enjoy using it too, so we consider it a very good investment.

As a new RE Agent myself, I am exploring the field everyday and enjoying my discoveries.

In my market, the difference between the cashflow for STRs and LTRs is not near enough to make up for the extra work involved with running an STR but we really enjoy managing our STR.

@Tim Mieney I enjoyed our conversation the other day.

As long as they do not exceed the maximum for the house (generally 2 per room), just let go and enjoy having a longer term renter

She has been an amazing tenant and I really enjoy working with her.

(Ex: comfortably dining, relaxing in living areas, etc) I have that maximizing living space, the area where the guests will be enjoying their stay the majority of the time, with amenities that fit in is the best bet for all!

And for the worst case if we decide not to buy in that market, we also spent time in a place we enjoyed anyway PLUS you would have gained some experience when interacting with locals, realtors, and other folks which will set you up for your next market you are interested in.Hope that helps.Mike