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Truthfully, I'd recommend something other than an 8085. If your goal is to show/develop software expertise, you can do that with your PC. If your goal is to make some sort of controller, there are many better choices than the 8085. The 8085 is just a GP micro with no onboard memory of either the RAM or ROM/PROM variety.
One of the reasons you're having difficulty deciding what to do is that you're going about it backwards. It isn't an erector or tinkertoy set that you buy and THEN decide what to build with it today and what else to build with it tomorrow. First you decide what you want to do then you DESIGN a way to do it. Once you know what your requirements are in terms of RAM, ROM, and I/O, then you can choose the appropriate device(s) from among a large collection of offerings. Almost any common device will have a cross-assembler or cross-compiler available so that you can work from your PC, and often an emulator capability as well.
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