First Time Home Buyer/Investor- Duplex House Hack Strategy/LLC set up- Will it work?

[Sam Samandar]

Hi BP community need some help here please... My sister and I are working to partner up for a real estate business. We both currently have W2s looking to exit to become full time investors. I have my primary residence single family home paid off in full Zestimate ~$500K, and no other outstanding loans for cars, schools, credit cards, and in good financial position with 2 years of reserves for expenses, etc. My sister had my parents' house passed down to her in a quick claim deed, which is also fully paid off Zestimate ~$420K, but she does have some "good debt", roof/windows for house $50K and car payments for her car and my mother's $25K= total debt $75K. I think she still qualifies for a first-time home buyer loan/benefit in Connecticut but not 100% sure what those are besides lower interest rate and potentially less % for downpayment? We have been contemplating our strategy to start our business by having my sister buy her first home locally here in Connecticut, a duplex as her primary residence and live in one unit with our mother, while renting out the other unit to a resident, and be able to also rent out her single-family house as a short term/midterm rental to traveling nursers/working professionals on furnish finder. My understanding is that she is required to live in the duplex for 1 year before she is able to rent it out and make it a rental property, is that true? or can she begin to house hack on day one of purchasing the duplex. Also, for the second part of the strategy, we would transfer the duplex into our real estate property investment LLC after year 1 and have my sister move back into the single-family house as her primary and rent out both units in the duplex as short/mid-term rentals. Does any of this make sense before I start to go down this path? My next goal would be to invest in out of state short term rentals and add those to the portfolio, but not sure how that would impact my LLC if I create a Wyoming Trust/Holding Company/LLCs and foreign file for incorporation into Connecticut to complete the first deal for the duplex, but then what happens when I want to invest in out of state investments deals/opportunities/homes? I know thats alot, but need somewhere to start. Right now, we are stuck on setting up our LLC/Structure in order to work towards this strategy and want to be sure we do so the correct way before getting started. Thank you BP community for your support!

[Jonathan Greene]

The LLC is meaningless in this equation at this point unless you are going to pay cash. You need a partnership agreement, but you can't buy in an LLC or transfer to an LLC without two years of tax returns for the business or a relationship with a local bank. From this post, I would say you are in the weeds.

You both have great starts with paid-off houses and limited debt so focus on the next step, not ten steps ahead. You will be in analysis paralysis forever like that. Figure out the first property you want to buy together and why, and start there.

[Sam Samandar]

Thank you for the information. I appreciate the insight on the requirements for transfer, and the advice on where to focus our energy next. 

[Aaron Ram]

@Sam Samandar Great to see you have interest in building a RE portfolio. It can get overwhelming with this much information at your fingertips these days.  I was in your shoes back in 2011 and this forum actually gave me a push to make my first investment purchase. I have a 10 property - 15 unit portfolio between Stamford and Bridgeport. Multis, SFs, Condos and short term. More than happy to offer any advice. Good luck with your journey Sam.