Timeline-Reading Order for
Rough Rider books:

RR Book 1 Long Hard Ride(summer)

RR Book 2 Rode Hard, Put Up Wet one year later (summer)

RR Book 3 Cowgirl Up and Ride one year later (summer)

RR Book 4 Tied Up, Tied Down one year later (late summer)

RR Book 5 Rough, Raw, and Ready seven months later (winter)

RR Book 6 Branded As Trouble eighteen months later (fall)

RR Book 6.5 Strong Silent Type six months later (late spring)

RR Book 7 Shoulda Been A Cowboy four months later (early fall)

RR Book 8 All Jacked Up one year later (late summer)

RR Book 9 Raising Kane falls between SBAC and AJU (early winter)

RR Book 10 Cowgirls Don't Cry immediately after epilogue in AJU (late fall)

RR Free Read Slow Ride immediately after epilogue in AJU (late fall)

RR Book 11 Chasin' Eight five months after CDC (early summer)

RR Book 12 Cowboy Casanova three months after CE

Timeline-Reading Order for
Wild West Boys books
(in Relation to RR books):

WW Book 1 Mistress Christmas ten months after Rough, Raw, and Ready (mid-December)

WW Book 2 Miss Firecracker two months after Strong, Silent Type (early July) and nine months after Branded As Trouble, two and a half years after Mistress Christmas