I recommend reading the book traction and following EOS - they have a one page business plan that is awesome to follow. any planner can work it's a matter of creating the plan and how to monitor and follow through with it which eos teaches

Quote from @Christopher Morris: Hello BP, I have been reading up and listening to podcasts on house hacking especially in NJ (Jersey City, Montclair, Bloomfield).

So inspiring to read about your success! 

And now with rates being high, plus many areas overbuilt with new apartment buildings, I’d be careful with unknown areas, and also what you read in the media about “hot” areas, up and comers, etc.I was in a similar situation to yours a couple years ago.

I remember reading about lots of trouble with private REITS. 

So I don't but if I did I wouldn't come away thinking it was a terrible investment, I would say it needs more time in the oven before I should even ask that question.My feeling from reading your description is it's a similar situation you're in.

What do you file for this "income overseas," do you file SChedule C self employed on your personal 1040 tax returns ?

After reading all of the replies, I think a cap is the way to go.

The Port Charlotte duplex...given it hasn’t suffered hurricane damage...could command a pretty penny on its own.I recall reading a piece in Forbes that suggests certain Florida markets could remain strong for years, which might help you gauge whether now is the right time to sell.

Registration and Financial Considerations for the Second Company:Is it possible to register the second LLC on the property (as part of the 50%-50% model) if it does not yet have an EIN (Employer Identification Number)?