I’m a new investor and looking to invest in a small multi family.

Answers: (1) The US legal system, that's why.     

I like TurboTenant for it's simplicity (and I'm pretty sure it's still free..)I have a client who is a smart-computer-guy not unlike yourself, he has a system for analyzing deals in bulk.

You could easily buy land that is zoned for multi-family and find a lot where you could build 4-8 townhomes.

I also purchased a multi-parcel farm property in TN where the trust who owned the property was out of money and needed cash to continue. 

I bought my first Multi-Unit (Duplex) and I'm gearing up to find my first SFH/Fixer Upper so I'm trying to build my list of resources for available properties in Atlanta and surrounding areas.

If it’s a multi rental property we ask for the PL sorted by property, which can be done with classes. 

Cross border taxation is very complicated, most developed countries like the US and Canada have sophisticated systems to ensure their residents pay taxes, and you are not likely to be able to achieve your goal of not paying Canadian taxes on Florida income while a Canadian resident. 

Read Dave Ramsey's book and i believe that will help you follow a system for getting out of debt and living below your means.

I create a comp set to dive into the competition and analyze how many other MTR homes there are, what cleaning fees are being assessed, booking lead time, # bedrooms and competition and if EV charge, Pet policy and Pools make a difference.JURNY for a PMS system & channel manager.