I have recently tried a Fender Frontman FM 212. Thats Transistor - but wow, the sound is nearly Fender Twin like, for 1/4 of the price.
The frontman series starts off with 15 Watts for 79,-€ here in Germany. They all have Headphone out jacks
IMO Marshall Amps are horrible.
A Squire Tele with 1 Humbucker in the neck position should be fine - but needs to be gut tested in the shop. If you feel comfortable with it - get it. Make sure you also test a standard Tele.
Happy rockin' birthday