Wife approved: $5K to spend! What first?

[Cap'n Hook]

So my 1972 Jimmy is a decent driver, but could use freshening of some major components. It has a 1988 Goodwrench 350 with TH-350 and NP205 all in need of attention. Was thinking along the lines of doing a Vortec head and cam swap, if the Goodwrench block is a decent block to use. The t-case is leaking, and probably needs to be gone through. Tranny would be gone through as well.

The brake system needs to be completely gone through, keeping the front dics, rear drums setup.

I also would like to get the air conditioning completely gone through and working again, along with the cooling system converted to electric fans.

Was also wanting to step up to larger wheels & tires (35x12.50x16 from the current 33x12.50x15) and do a 4-6 inch Skyjacker lift. Would I need gears front and rear with that size tire?

So basically is the engine upgrade, tranny & t-case rebuild, brake system, A/C rebuild, cooling system upgrade, wheel & tires, lift, and possibly gears front and rear do-able for $5K?

I'm pretty sure I can do most of this myself with the exception of the A/C, brakes, and gears.

Also, is the 1988 GM Goodwrench 350 block gonna have a 4 bolt main, or would I be ahead in purchasing a new block?