30 hotel rooms a year is pushing it IME. I'm not saying bacchi didn't do it, just that it would be work and probably not hotel rooms in big exotic cities.
Yeah, that was off the cuff. It'd be mostly road trip hotels and it might not be quite 30 nights. Let's try.
** This is ad lib and may not be the optimal strategy given the limitations with Chase and Citi. As it's quick and dirty, it's as trustworthy as the time I've spent, which isn't much. **
Given $27k of annual spend,
Month 1:
Chase CSP -- 50k UR points transferred to Hyatt for 3 Category 4 nights (Grand Hyatt Seattle, ~downtown) -- $0 AF waived
Month 2:
Chase Marriott -- 80k points for 1 night at the Central Park JW Marriott and 2 nights at some interstate Residence Inn -- $99 AF
Month 3:
Barclay Choice -- 40k points for 2 interstate hotels (with breakfast) -- $0 AF
Month 4:
Chase Hyatt -- 2 nights at any fancypants Hyatt worldwide -- $25 AF the first year
Month 5:
Amex Hilton -- 80,000 points, worth 2 nights at several Manhattan Hiltons -- $0 AF
Month 6:
Chase IHG -- 60k points for 3 nights at any of the 100s of IHG hotels on the road -- $0 AF waived
Month 7:
Citi Hilton -- 75k points for 1 night at a SLC Hilton and 1 night at a Moab, UT Hilton -- $0 AF waived
Month 8:
Barclay Arrival+ -- $500 for 2 nights at $250 hotels -- $0 AF waived
Month 9:
FNBO Best Western -- 50k points for 1 night at West Yellowstone and 1 night on the road to Yellowstone -- $0 AF waived
Month 10:
FNBO La Quinta -- 1 night after 1 charge -- $0 AF
Month 11:
Citi TYP -- 30k points transferred to Hilton at 1.5x giving us 2 nights on the road (or 2 nights in a suburb of Seattle) -- $0 AF waived
Month 12:
CapOne Venture -- $400 for 2 nights at $200 each -- $0 AF waived
Total outlay: $124
Total nights: 25
--Total fancypants hotels: 5
--Total destination hotels: 5
--Total interstate/suburb/airport hotels: 15
Total spend: $25,000
Other costs:
-- applying for a card every month
-- swapping out the spend card every month
-- keeping track of annual fees and dates in a spreadsheet
You probably don't have 25 days of vacation a year anyway so modify as desired. It'll reduce the work.
Eta: Source is
https://docs.google.com/spreadsheets/d/1UEWoLQ3JqVIwHPRuXYuGw13pI5bzQ1C6f37q6RU1idE/htmlview?sle=true