Good questions, but what is "right" for one person is not always right for the next, so ultimately you have to decide what is right for you.
As far as pedals vs. built in or multi-effects, keep in mind that with built in effects, you usually have to develop presets or patches that combine the effects in a way that doesn't then allow on the fly changes - unless the particular amp also offers a pedal that allows on the fly changes (like the Boss Katana). Even then, you probably won't have as much flexibility as with external individual pedals. What is best for you is determined by the level of flexibility that you require. If you are doing live performances of a broad variety of songs or music styles, individual pedals may be the best answer, but that can also be cumbersome to haul around. If you can be satisfied with a handful of presets that meet your needs, internal effects may be the answer.
Since you already seem to have a set of pedals that meets your needs, I think your concept of using them with a small amp is a good approach. I would recommend that you choose one that has a built in effects loop though, as some effects behave (sound) better in an effects loop than in front of the amp. One possibility would be the aforementioned Quilter 101 head if you are not familiar with it. They are an excellent sounding amp that does a pretty good job of tube amp emulation and dynamic response, is very small, light weight (2#), and has an effects loop and multiple amp emulations. Power output is continuously adjustable from nothing to 50 watts (100 watts for 2 of the amp sims), headphone jack and output jacks for both 4 and 8 ohm speakers. Mine sounds awesome connected to a 12" Cannabis Rex speaker, and as I said before, seems to be a super match up with a Les Paul. It works with pedals on the input and/or in the effects loop very well. A really good setup for anything from low volume home practice to a gig setting - it will get very loud. I really love it, but honestly do not use it as much since I got my Katana - primarily because, for my use, all I need are a handful of presets that I have dialed into the Katana and I'm good to go. If the Quilter interests you, I would sell it to fund my '59 Tweed Deluxe amp build in progress
which is a whole different story.
I like the approach of a separate head and speaker, as it provides the flexibility to try different speakers or use different sized speakers as the occasion calls for.
There are many other good ways to skin the cat of course. The new amps in pedal form that are now showing up may also be an option for you - there are quite a few of them now. Do you have a budget in mind?
Tom