The only thing holding me back is talking to someone who has completed the course and is successfully making a career out of it a few years down the road.

I'm borrowing at the rate of ~7% and 7% is a great return to me, especially with the stock market near all time highs. 

Any tips or pointing me in the right direction will be greatly appreciated.

Hey @Eddie Miretsky, I am in MA myself, but in the Northshore area.

The problem is, airbnb income is not considered "stable" so for qualifying purposes there isn't a way to project that accurately if there isn't any previous rental history for the property. 

If you are close then just go to office and pickup the check.

If I buy a vacation home using a 2nd home loan and rent it as an AirBNB when I am not using it, can I still do a cost segregation study to accelerate depreciation and offset losses against my W2 income if I follow the rules of STR tax loophole (I.e., the average stay in the house is less than 7 days, I manage the AirBnB myself, and spend 100 hours or more a year and more time than any other person/entity on managing my AirBnB business)?

You'll get the most exposure using an agent.

While I don't see it on the IRS tax information, if I remember from the conversation with him, I think you have to buy properties that need significant improvement. 

Take off the party hat 🥳😔The recent decision by the Federal Reserve has sparked widespread enthusiasm across markets.