It seems that for now, your best option is to start off with an affordable, trailerable boat and deal with all the associated downsides of trailering . . . and there are many. But, this approach works for many young families, including ours - a few years back.
When a stronger and steady income frees up some "disposable" income for a cruising size boat, you can decide if leasing an outrageously expensive hole in the water is worth it. If it's any consolation, we were paying over $8,000 per 5 month season, for a 36 foot slip (including winter dry storage).
True Blue . . .
sold the Nauticat