I just want software I can keep everything in so I'm not fishing around notebooks here, spreadsheets there, etc.Thank you!

You may find some hard money willing to loan on the deal if you do some fishing.

Ultimately this will simplify your life and make investing a more hands-off ordeal than fishing for a real estate agent to bring a tenant each time you have a vacancy.However, if you are PM averse, Zillow Rental Manager is your best single-stop for procuring a ready, willing, and able tenant in my experience.

Hint: if someone ask you for a POF, you are fishing in the wrong pond. 

Lastly agree though if your going with large group Airbnb is much better than hotel and better bang for the buck.. or if I go to say Montana to fish hotels are not very nice so the airbnb we use there is pretty cool and worth the money cheaper than the hotel and right above a wine bar  so that's a plus.

Plenty of fish in that ocean.

Fish tacos aren't as appetizing after that trip to Maui.

Some people are just fishing for a "deal".

People always value being on/near water.In the Chattanooga area we have Lake Chickamauga, which is well known for its bass fishing (and the related STR demand!). 

Teach a man to fish something something...4.