First Deal Done! Ready to scale, but uncertain

Hi everyone! I'm trying to weight the risks of purchasing another property to add to my portfolio.

I just got my first deal done last month, a SFH and just signed an 18-month, healthy cashflowing lease. Mortgage is $1450/mo.

Now, my siblings and I partnering on a duplex together just up the road. My portion of the mortgage if vacant is around $800/mo. We are inheriting an existing tenant, however, we're confident this deal can rent out and cashflow positively especially once our reserves are full (we're putting 10k aside from the start and this is very turnkey).

My next deal is already sourced, a house hack triplex. Mortgage on this one would be $3.7k per month, and after I move out it will slightly cashflow at 95% leverage (using a 5% downpayment) after putting money aside for repairs and management. Once I recast at 20% equity and get rid of PMI, it will be much more profitable.

My fear/hesitation is if everything goes wrong. For example, if I lose all my tenants and my job.

I'll owe approximately $6k per month for all my mortgages, which is a lot given my 8.5k per month salary (after taxes). I do have enough cash reserves (transparently a lot in the stock market) for around 1 year of this worst case scenario AND IF I lose my job and need to get a new one. If you add in other living expenses, it brings my emergency fund to around 6 months.

I know I'm in a really strong position, however, just the thought of potentially owing $6k/mo in mortgage is quite daunting, especially if I suddenly lose my income. How do you know when it's time to bite the bullet and just go for it and take on that risk?