Suggestions for an Analog Front-End

Rega, the table you can throw in the pickup drive around all year and when you need it it will just play and never mis-track. Never thought of it like that but now that I do yeah that would be Rega. ;)

Spend more on the table and cartridge and pair it with a less expensive phono-preamp for now. I can upgrade later if desired. Open to other strategies.
Glad to hear because its always good to have a plan and that is a good one. One of the great things about analog is if you buy right you can buy for a very long time. It doesn't obsolete itself every 18 months like digital. A good turntable will last a very long time. A good arm maybe even longer. 

I have no advice on specifics, only to keep thinking like you're doing. Because you just never know what you may find. You may come across a killer deal on a super table, then run it with a cheap cartridge or stage for a while. Or you may find a killer deal on an arm, whatever you get the idea. 

The phono stage will be the hardest. Its just a very demanding component, hard to get right when on a budget. Yet when you do get it right it can be night and day the difference it will make. 

Another consideration, my experience would have me leaning towards arms with connected phono leads over arms that use RCA and interconnect. In my experience the phono signal is so delicate you wind up spending big money trying to find an IC good enough to make up for what is lost in the extra connections. Sorry I know that sucks because a lot are built that way but it is what it is. Also the last thing you need in the budget range is having to buy more stuff like a phono IC.