Ls Hay-welcome to HT. Not sure where you are in MD and it is a really variable state. However, if you are montgomery co west, your conditions are really similar to mine. That said, here goes-
I started out small 25 years ago with equipment that someone else had worn out twice and would not do that again. Hard to make horse quality hay when everything is breaking down on hay day and you are running to get parts, repairing or waiting for an emergency tech to come fix something. I am not saying to forgo used equipment at all but think ahead. I worked up from 15 or so ac to over a hundred while doing a very full time job but now in major retirement I am down to 25 ac so very similar to you. My suggestions to you-
don't get greedy, never cut more than you know you can handle at one time. Repeat after me... This rule also saves you from loosing the whole enchilada to rain that was not forecast. I would go with kicker wagons. I am not saying the other things won't work but if you are relying on you, yourself and you, it is the best bet. Never let a bale touch the ground other than flyers over the wagon and minimize those. Get larger kicker wagons that will fit under the rooves you have-measure to top of rack and add 24-30 inches for bales that stick up (otherwise, you have to get up and toss off some bales on top before you back in.
Stolzfus in Honeybrook PA makes good steel wagons-get the truck tires, not flotation tires. they are reasonably priced. I would get 8.5 x 22' wagons. You will find that the 950 (I had one for a long time) even with larger rears just does not have the butt to back those wagons and you might want to consider an upgrade to 50-60 hp like a JD2440 or 2550. both good tractors and could be used in a pinch to run the baler to finish or whatever. you should be able to get 175 bales or so on the 22' wagons with a little skill with your thrower.
I would suggest you look at a Krone 2801CV disc mower conditioner. Just moved up from a NH1409 roller machine and like the impellers-I do all grass-orchard with some timothy mixed in.
The Krone 4 basket tedder and the small rotary rake from Krone-38t are well matched to your size of operation. Messicks in PA handles Krone, probably others as well and I think they have a shop in Gettysburg or Carlisle pa if you are in the west central part of MD.
For balers, a NH 570 with a 72 thrower and hydraulic tension is a nice set up-nice controls/hydraulics at your console for thrower speed/distance and direction of throw. The number of wagons is really dependent on how many bales you want to make at one time. I would suggest you start with 6 ac per batch of hay cut and see how that works for you. that is 700+ bales in wagon capacity and don't plan to empty them the day you bale. Your objective on baling day is to get them in wagons and under shed roof. Anything more is a bonus. I get 100-140 per acre depending on year moisture and temperature and i fertilize well per soil test data. ISF makes a slick 5 gal tote preservative applicator that uses Hayguard that would work well for your operation.
Lastly, as far as marketing-moving hay-line your customers up during the winter, like as in now. Try to get customers that will take your wagon (or you tow it to them) and they unload in their barn. That way you don't have the extra expense of handling and stacking. you might have issues marketing that much hay in advance of any product to show with no track record so be prepared-even if you plan to make less the first year to get your feet wet. It's a journey and an adventure. Hang on and enjoy the ride. HTH
Some other things you will need-10' pull type bushhog for trimming fields, 3pt hitch 600# fertilizer spreader, access to a NT drill for over seeding fields. Contract your herbicide application, bulk fertilizer, and liming to the local coop.
Oh, and for what it's worth, you don't need a round baler. You do need someone local that you can get to roll stuff if you loose it to rain etc. You just don't make enough on round bales around here to make numbers work unless you are way bigger than you are. I had a good JD457 RB as a back up and sold it after 5 years and about 250 bales through it. Just could not justify something that expensive sitting in the shed taking up space and rusting for the privilege of saving a few ac of hay every several years. mostly I used it when I ran out of kicker wagon capacity. much cheaper to buy another wagon