What to do with parents house?

[Evan Fine]

Hi Everyone,

Quick background about me, I'm 25, just starting out in REI and interested in Buy-and-Rent strategies, something long-term to build wealth as I have a full-time job. Currently I rent in NYC. My dad and my brother stay with me Sunday - Thursday and go east to Long Island Fri - Sun to hang out with my mom at my parents house (mortgaged).

We have definitely outgrown our current house but my parents are not savvy in RE so it's up to me to decide where to go from here. After doing some research the local market it looks pretty saturated with not a lot of movement (buying/selling).

I'm thinking of investing ~20k (currently worth $350-450K, prime location) into the house to bring it up to rentable condition (~$3.0-3.5K/m), and buy another house for my family to live in (and rent out in the future?).

Any suggestions what you would do or what questions you would ask yourself in this situation?

Thanks!

Note: Current house details - Private Village (private security / town hall / 2 parks / 2 beaches / boat ramp) - ~$3K taxes annually - 2 story with basement - 4/1 - detached 2 car garage - 9k sq ft lot - Grade A Schools k - 12 - Safe/quiet neighborhood - Close to big university (not interested in student rentals though)

Note: Village is divided into 3 sections based on house/tax size. Biggest section has multimillion dollar mansions and taxes around ~$20k, while the smaller section tends to be houses $200-400k with annual taxes around ~$6k.