if you purchase through Disney, it will sell you only your current use year unless you purchase the minimal points required to be purchased a new rather than existing
DVC member.
Getting a different use year is the same as being a different member. You get separate annual statements, your dues are billed separately, if you do automatic monthly withdrawal from your bank account for dues, they will be taken in separate transactions, you will have separate banking dates, and the points from one use year cannot be mixed with the points from another use year to reserve any one single night. To combine the points for a single trip, you either have to transfer points from one use year to the other, or instead book some nights with one use year and the remaining nights with the other and then have MS link the reservations so you do not have to change rooms. in that situation, you would still have two separate reservations when it comes to when you can first make restaurant reservations or do FP+.
We have two use years and do not consider it difficult, confusing, or a disadvantage. The advantage is that we can avoid having trips in the last four months of one of the use years, when you risk not being able to bank points if you have to cancel, by booking using the other use year.
As to two resorts, that is mainly the 11 month booking issue. Do you want another resort and room classification that requires booking 11 months out, e.g., boardwalk standard view? We have two but followed a rule that we would not purchase a second resort until we had enough points for one resort to get a 2BR for a week during magic season at 11 months out in any given year since that was usually our minimal stay and room category that we wanted once a year.