If you want to go from the simplest gameplay the most complex gameplay, go by release date. Reach is definitely a good starting point into the series, and in terms of the chronological order, its technically the first one to play. If you actually start from Halo CE on PC, you dont have to wait for the reach port.
Does reach come before Halo 1?
Reach takes place in a futuristic science fiction setting; the year is 2552, shortly before the events of the video game Halo: Combat Evolved, and during the events of the novel Halo: The Fall of Reach.
Which halo should you play first?
Start with Halo Reach, go on to Halo: Combat Evolved than to Halo 2. Move onto Halo 3: ODST and than finish with Halo 3. I dont recommend moving onto Halo 4 as it really goes down hill right after, but if you really want to, start with halo 4 and move onto Halo 5: Guardians.
Which Halo is hardest?
While theres a case to be made for most of Halo 4s levels being the hardest of any title in the Halo series, the games final level titled Nightfall is considered to be one of the most difficult in this entry. Unlike every other Halo 4 missions, Nightfall is fought solely against Prometheans.