Hoping to hear from fellow younger investors in MA who live in these expensive areas as well. 

Level 1 is to cover your living expenses.

Bringing techs in-house definitely offers control, speed, and potential additional revenue streams, but like John mentioned, it comes with more management and liability considerations.For smaller PM groups or those still growing, partnering with reliable vendors and building long-term relationships can often deliver similar consistency without the overhead.

I second the house hacking idea as a great way to get started and reduce your living expenses. 

This means your income stream can rise to match increasing costs, while your debt service—if you have a fixed-rate loan—remains constant.

It is crucial to research whether the property value will be reassessed upon purchase to avoid underestimating expenses during the underwriting process, as some US states reassess property values when real estate is sold.In addition to reducing expenses, we also explore additional income streams.

No don't do that if you cross streams of rental income (all income goes into one LLC) then all your future income is at risk of loss.  

My guess, without knowing exactly where you're located or what your local market is like, is you could refi this, use the funds to invest in two more properties, and keep around the same cashflow, but you'll then have three streams of cashflow that are growing and three properties that are appreciating.

I'm considering trying out Prop Stream to try going direct to seller. 

It’s a certified men’s recovery residence operated through Vanderburgh Sober Living, designed to provide safe, supportive, and structured housing for men in recovery.