Struggling real estate investor

[David Manning]

Hi!

Really need some opinions from some experienced real estate investors and this seems like the perfect place(glad I found bigger pockets! 

I have 2 rental properties(a 2 family home that I bought 9 years ago that needs new roof eventually and a short term rental a few hours away up north that has a 5.2 rate and is very updated) I used a cash out refi in 2021 for the 2 family to take out 25k(and it lowered my payment, went to a 3.2 rate for 25 years for the 2 family) and then used that 25k to buy a 240k cabin up north to use as a short term rental and family vacation home.

2023 was the first full year for the cabin and it brought in 25k, however expenses were 36k, so 11k in the negative. The 2 family was +3k so that helped off set. I expect the 2 family to bring in 6k this year since the escrow amount lowered 225 for me and I am increasing rents. 

If the cabin doesn’t do better than-11k I might have to sell one of these investment properties. Best case scenario this year between the 2 of them I break even with rental income. Things are tight with day care, mortgage for personal home, and kid #2 on the way. I have an 8-5 that brings in just under 100k and I work as a part time realtor(sold 3 houses last year and had a rental deal too) and I bartend most Sat nights(300 a night, working 4-11)

If I sell the 2 family, after 15% cap gains and 2% to the buyer agent and lawyer fee and pay off all our debt(wife and myself, not mortgages) We would have about 150k left over.

If I sell the cabin, after agent fees and cap gains we’ll probably walk with 60k.

Would keep pushing forward? Sell the 2 family? Sell the cabin? 

Thank you!