Which gap in my collection should I fill first?

[93EXCivic]

I have a collection of 13 watches right now (and plan on adding a few more this year, couple more Vostoks [NVCH-30 reissue, Steve Zissou and a dateless vintage blue scuba dude if I can find one) and some builds) but I feel like I am missing three big things from collection, a chronograph, a dress watch and a grab and go quartz. I am going to be saving up a little to buy something nicer then my usual stuff in one of these three categories. It will be in the $400-$600 range and vintage except the grab and go.

Which gap would you fill first?

For the chronograph, it would be either a vintage Strela or vintage Olma.
For the dress watch, I was thinking a vintage tank or something from Longines or UG. It will be a two hander or maybe a sub-dial second.
Grab and go quartz I have no idea. I am leaning away from vintage and more towards something newer because I'd like watch resistance (water resistance being not having to worry about it in the rain). Basically I want a watch that could be used anywhere except with a suit. So thoughts on this one would be great. Pre-owned preferred.

I have a few quartz watches but two are not all that nice and the other two are beaters. I have an Olma which functions as my current dress watch but honestly I don't really like it as a dress watch more of an everyday watch to me.