I don't want to hurt their feelings however, this will require a lot of logistics on my part to make this purchase happen.  

I'm going to run some details by you and I'd like all of you who feel you are qualified to advise me so I can learn how to properly analyze these deals and be more cognizant of potential pitfalls/mistakes:So, I found this property off market in a Chicago real estate investment group.

@David Zhu I host a meetup in Los Gatos.If you interested in out of state multi family feel free to check it out :meetup.com/Los-Gatos-Real-Estate-Networking-Meetup/

Feel free to reach out to me anytime.

@Christopher Walrod if your personal situation allows you to house hack it can be a huge shortcut to becoming a real estate investor.

Having trouble analyzing this deal as there are so many variables and I do not have the experiencing analyzing deals to make me feel comfortable taking the risk.Purchase price of the land would be $250,000 not including closing cost or fees, and construction for a new 3/2 home with an attached 1/1 ADU is estimated to cost around $300,000 - $400,000 finished.

For the best rates, consider working with a company like ours, which specializes in real estate funding and can guide you.If you're ready to explore these options further, feel free to connect!

Feel free to send me a PM if you want to discuss market rents etc. 

Seen some nice places there on AirBNB but feel like a… fish outta water… when it comes to carribean/international investing?

Personally I would pick option 1 because you cash flow is already high and so a slightly lower cash flow with higher LTV has relatively minimal impact on cash flow.