When is it time to sell an investment?

[Jobee Vincent Buenaventura]

I have a 2-family property in NJ that can potentially sell for $500k according to comps given to me by my realtor.

I bought it in 2020 for $390k. In 2021, I cash-out refinanced and it appraised for $450k. I used the money for the down payment on my current single family residence. As of now I owe $350k on the loan.

I net around $500 monthly but I am thinking of selling it in order to use the funds to get experience working with a private lender/hard money for home flips/BRRRR. I also have a headache tenant that I inherited from sale that I can't get rid of just by not renewing the lease due to NJ tenant law protections. And they're careful enough not to royally f-up our lease agreement.

So my gross profits would be roughly $150k but after commissions/fees and capital gains tax it seems I’ll net perhaps just above $100k.

I feel like my property has already appreciated by a good amount. So I’m on the fence of whether to keep the current cash flow or sell and then reinvest whatever Uncle Sam or the brokers didn’t take from me. Would $100k+ be enough to delve into the world of private lending/hard money?