You don't need to be a server owner to see that it CAN be profitable. Just go to any server's website and go to their donate link to see how well they're doing. This will give you a good idea of what types of servers are doing well.
The EULA is not really enforced but people seem to follow it regardless. According to the EULA you can't sell game changing items. So cosmetics and things such as an extra /sethome should be fine. Bukkit is still a thing. PayPal pretty much has a monopoly on online transactions, so you're stuck with them. Chargebacks are as annoying as ever. To combat them just have an ip ban policy on anyone who attempts a chargeback. Obviously still return their money, but just ban them so you don't have to deal with them. (Also I thought PayPal refunded fees if you just contact them and tell them about the chargeback/situation)
If you're not in it 100% for the money I'd say go for it, I understand that it can be fun managing a community. The small profit is just icing on top.
Also, Thank you for your service!