However, after doing my research and talking with a few people, I've been feeling SUPER overwhelmed.

An investor friendly agent can do all sorts of helpful things, like setting you up with a search for properties or connecting you with folks who have recently done deals like the ones you want to do. 6) Consider analyzing a deal or two in your local market, just for practice, with a free use of our Rental Property Calculator (or other calculators).

Feel free to reach out whenever!

@Travis Andres @Brian Malavsky If you're looking for AI messaging, my team has developed an in-house PMS that is now public called Hostvana (hostvana.io) who's core competency is messaging (along with free lock integration and other features) and is more advanced than Hospitable's for a very affordable price.Here are some recent replies in my personal account inbox:https://ibb.co/nk8KWbR (cleaning fee policy question)https://ibb.co/sgP0qmr (parking question and check on status)https://ibb.co/HCKVPd8 (random question answered with previous context)https://ibb.co/gv0tY16 (early check-in reply after checking calendar.

I also don't like how long it takes for the checks to clear I do use the free version and takes about 5 business days to clear. 

(This is the part that Im not sure is dumb or not) For two years while I'm living at home rent free, if I'm able to charge $2.1k each unit for rent, I would be left to pay $600 out of pocket to cover monthly payments.

The residential manager acts as a defacto PM, but they occupy one of the rooms for free, so run your numbers.

ESA's generally are not service animals and these are generally fake certifications that are abused by people to get free accommodations for their pets.

Even if the tree sits on their side of the property you are free to trim the trees that overhangs on your side of the property any way you like.  

Both are free (included in subscription) and use Stripe to collect payments.