If money is really tight, I'd suggest taking a look at anything other than a Kubota or a Deere....great products, but the two most expensive you can buy for any given level of performance. When I priced out comparably equipped models from all the big brands I would have had to pay $10K more for a Kubota, and a Deer would have been a bit more. Other brands are sold in package deals as well. When I settled on my LS, I looked around the country and saw that a couple of big places, like RCO in Tx, sold packages that were attractive. I'm sure you could find the same for a variety of brands.
One small note...WA has a use tax, so even if you buy the machine in Tx, you very likely still owe the use tax...not easy to enforce, but it's become a sticking point, and some folks are getting busted for it.
For the size property you're talking, and the description, I can't imagine you'll ever have a problem with an HST unit wearing out, or breaking...if you did, it would be a freak. That also brings up the issue of warranty....some brands offer a considerably longer warranty than Kubota. Kioti offers 4yrs, Mahindra and LS have a 5yr powertrain warranty...just something to consider.
For the work you're describing, the HST will be more convenient, and won't hinder your ability to do things...you're not pulling a hay bailer, or plowing large fields, so the power loss to HST won't be noticed. It will also be far easier for folks not so accustomed to manual transmissions....especially because with a tractor there are a lot of other things you're minding....the level of the implement, the throttle position, etc, etc. My wife has driven a standard transmission for years, but doesn't want to drive any of my tractors except the one with HST. Personally, I think she needs her own SCUT