I know that i could buy my next multi family property as a primary residence close by move in, rent half live in the other and than rent where i am now which would cash flow upwards of 1k monthly, or i could buy another multi as strictly an investment property out of state which would be a lot cheaper (taxes and cost of property) and a lot more landlord friendly laws than New York, i guess i’m just undecided on which route i want to take and I’m trying to weigh the pros and cons of each scenario.

Anyone in business takes risks, but a lawsuit and some other things don't look great.

My understanding of Avalara is I still need to input the info so it would take 10-15 minutes to do.

Take it slow, and you’ll do great.

Instead I want to take advantage of the opportunity I have of living rent free to invest my time and money in STR's to hopefully build that portfolio up and eventually make that my main source of income (I understand that will take time).

This may take some work. 

.🔹 Afraid to let a property manager take over?

Commercial deals take longer and are all about relationships, so connecting with investors, brokers, and property owners is key.

As everyone said, 20% is fair for a manager to take care of a STR.

Highlighting the strong profit potential and taking measures to address any concerns about costs, scope, or holding risks will make this an even stronger pitch.