Whatever you buy, make one of them pro grade. Then in three years do the same thing. Eventually u will have a lifetime's worth of equipment. Regarding the cheap stuff; it worked for me when I could not afford Anything better. But trying to START the cheap power equipment!! On my God!!! Never again! I have Exmark and Stihl now and life is extremely comfortable.
He has 2k to spend he doesn't need to buy anything low end.
Craftsman is low end
Mtd (home light, murray, troy bilt, much more) is low end
Ryobi is low end (sorry carscw it is considered low end even if you have good luck)
John deere is low end
Some toro is low end
Some toro is middle grade
Honda is middle grade
Echo is middle grade
Shindawna (spelling) is middle grade
Husqvarna (spelling) is middle grade
some stihl is middle grade
Some stihl is high end
Commercial grade equipment is high end.
Pretty simply put many many more brands are catagorized as mtd. And for 2000 he can afford a nice set of equipment this is why I recommend a honda he will get years of use if he maintains properly they are easy to use and for .5 acre more than enough mower. He could get a echo pas of any power head will do good for his garage space one machine to maintain and use. The attachments he could get all now or one at a time over time as he needs them. These two machines coupled with a hand held blower and he will be in good shape. He really doesn't need anything more high end than that unless he's going to be putting tons of hours on them or beating the hell out of them. He doesn't need cheap crap he needs to replace over time because his starting budget is more than enough for good stuff. He says he went with a hrx and a stihl multi tool he's in good shape.