Yes, lots to consider. If it were me, I'd get that cover off the pool. I'd buy a new LoopLoc, Merlin or similar mesh safety cover. I'd also have a pool company close the pool. By closing it I mean pump out/plug the lines to make sure there is no water in them, and add antifreeze. No need to add chemicals to the pool. It's already green. Then around April 1st, take the cover off, and replace any needed equipment and
SLAM Process the water. Within a month you should have new equipment and crystal clear water, which is before swim season starts, unless you have a heater. Without a heater, my swim season is Mid/late May to end of September, though I have a cover I keep on the water in the shoulder seasons to reduce evaporation (and therefore keep heat in). Your pool was closed last year, but I would never expect plugs to keep water out of the lines for more than just one winter. The potential issue, broken underground pipes, is too serious.
That said, you still have time to replace equipment now and SLAM the water clear before closing clean, IF you hop to it immediately. Just depends on your priorities. I'd focus elsewhere til spring. One of those fall projects I'd tackle is trimming back/removing some of those trees near the pool. Trees and pools don't make good neighbors.
One thing to note is that MD has a variable speed pump rebate of $400. There is no reason to buy a two-speed pump with that type of money available to offset the extra cost. Never consider a single speed pump - dark ages. You do need to pay MD sales tax to get the rebate. So you can get it through a pool guy or buy it on Amazon, etc., as both should charge MD sales tax. I however, in order to make my life more difficult, purchased it from the cheapest vendor I could find online in another state, who, as I would expect, did not charge MD sales tax. So I needed to "convince" the MD rebate folks that although I didn't pay sales tax at the time of purchase, the fact that I filed a Use Tax return for MD, remitting my own tax payment, fulfilled my MD sales tax obligation, I have fulfilled that requirement. It took some work, but I heard back last week that my rebate was approved, so I can vouch that they will accept that approach if it applies to your purchase. My net outlay, including sales tax for a smaller sized VSP (1.85HP) was about $460. The "full size" VSP's are 3 HP, which, if your pool has no water features or spa, doesn't really need, though no harm except price to get the larger one.
Like Maddie said, let us know what your priorities are for this fall and next spring.
