Have done all 3 as well. Bit of a summary:
-Saba - deep diving at the best sites, all boat diving, currents can run, very limited land-based opportunities, no beaches, limited dining options, no shopping opportunites (lace and saba spice aside).
-SXM - decent shallow sites to deeper further offshore sites, very little to no shore diving, most land based opportunites, most active night life, wide variety of topside beaches, excellent shopping opportunites on both Dutch and French side, great restaurants at every price point. Probably the largest inventory of properties available from hotel rooms to Villas with staff.(Warning - January will be high season - crowds, traffic jams, bridge openings, mega yachts, celebrity sightings possible and it can attract a bad element.)
- Bonaire - shallow to deep sites, boat and shore diving, reef close to shore, some land based touring options, no 'real' beaches (ironshore), no crowds, little traffic, plenty of restaurants at all price points, dedicated to dive 24/7, few trinket shops downtown...and Gio's for gelato which makes the entire trip worth it!
All three offer easy on the wallet lodging options, SXM and Bonaire require a car rental (you could get by without, I prefer having my own car), Saba uses taxi services. SXM and Bonaire apartment/condo/houses with full kitchens allow 'dine in' options to cut down expenses and both have great grocery stores.
If it were me, Bonaire. Great for beginner-wanting-more in an almost pool like environment. Stick to shore diving, eliminate the boat fees or add on later - operators are very accomodating. I'd look for a place on the water to try to log as many dives and build up the confidence of the less experienced diver. (That was me a few short years ago with a very experienced patient buddy!) If the $$ for the larger full service resorts - Plaza, Divi, Buddy, Capt Don's - exceed budget, look into Sand $$, Bruce Bowkers, Black Durgon. All are on water and either have on site or next door shop. All have great house reefs, close to shore, easy diving, lovely sunsets.
Not sure what flying out of Wisconsin is like, but Continental has Houston - Bonaire red eye. In any case, from anywhere, airfare is expensive. Good luck!
