20$ vs 300$ does not really matter if you have multiple 10K MRR.
Why would you change where you live if it works?
moving from self hosting to a hosted service gives me other advantages. whether those matter depends on the specific situation. the reality is that in many cases the hosting costs rise faster than the costs for self hosting would, and big companies save lot of money by moving back.
switching from $20 a month to $300 a month is only worth it if i save at least a day of work per month. but that's often not the case. and the more you scale up the less work per revenue/profit you have.
the one big advantage of paid services is that they lets you scale up faster. if that is what you need, then sure. OP does not scale fast.