Totally do-able because I have done it.
I Bought a Grampian
26 North of Toronto, Ontario
with trailer/5 sails/outboard/ PFD's Flare gun et al etc for $800 Cad/ $600 Usd.. This boat was lonely so I acquired 3 more for the price
of free to $300.including cradles etc, some sails
etc etc .
Remember old sails
make great laptop
bags etc to market on your channel ...
Taking the best of the best & selling or recycling the rest.
economics is a very good (free) boat& two trailers & cash for upgrades.
There is no better way to know your boat; than intimately....
"Sweat equity is still cheaper than sitting in a bar"
Note of caution; Make sure to search there is someone local to take your scrap especially the plastics/Fiberglass. can be a costly disposal.