Objective
My objective is to rebuild my trusty 305 so that it makes 250hp and runs on 87 octane pump gas using stock/GM components to reduce rebuild cost and maintain reliability. This engine is intended to be installed in my 1987 Scottsdale and make daily driving more interesting and extend the life of the vehicle. I plan on driving state to state and Im more interested in drivability than wild loppy cams and high top-end (my trucks speedometer only goes to 85mph).
*Did I mention this is my first engine rebuild?*

Short Block
I currently have a LE9 305 (engine code H) and stock TBI induction attached to a TH700R4 transmission, unsure about the gears out back.
Displacement: 305 Bore/Stroke: 3.736 / 3.480 Lobe Lift IN/EX .2484 / .2667 Compression Ratio 9.0:1
* To limit down time, I may rebuilt a 305 from an 84 Caprice Wagon. Its a LG4 (Engine code H)

Cylinder heads
GM Vortec Heads w/ 1.50:1 Ratio Rocker Arms, 64cc combustion chamber, 170cc intake runner (I’m not sure what this will do to my compression but Im pretty sure it will work)

Camshaft
The following cams are designed for TBI engines and are 50 state smog legal.
Edelbrock   EDL-3702 Duration: 194/214 Lift: .398/.442
Crane Cams CRN-114112 Duration: 194/204 Lift: .401/.423
(Should I be looking for a different cam?)

Induction/Ignition
Holly 670CFM TBI p/n 510-502-5 I’m considering a GM 2 barrel TBI from a 454 as a low cost solution.
Initially I will be using a stock GM HEI unit and I will be using the stock GM computer with a custom chip from either: Fastchip.com, Hypertech-inc.com or Superchips.com (Any recommendations, could I program it myself?)

Exhaust
Edelbrock TES Tubular Exhaust w/ high flow cat and Flow Master Series 40

Future Test Results
Hard to tell, my trucks stock HP is 170@4400 and my Torque is 250@2400 these numbers are far from impressive. If I could add 80 horses and 50 more ft. lbs. torque on a budget. All while using what I have, it would put a smile on my face.

I realize that most of you do more aggressive builds and I hope I’m not wasting your time with a “better than stock” build; but I would like your opinion / advice on these components. My level of knowledge in engines is fairly entry level. I’ve learned a lot from online sources as well as Chilton & Shop Manuals and doing my own work.

Take a peek at my Scottsdale over at http://www.cardomain.com/ride/340557  

For a high torque 305 in a Scottsdale, you're making the right choices.

Actaully with the cam selection, Vortec heads, and a 670 CFM TBI this will probably produce something more like 300 horses at the crank.

You'll have to rechip the computer, just Google it.

Since your changing heads, cam, intake, and computer chip; why not put a 350 short block under the heads? Probably won't cost much if any more.

Expect to rebuild the tranny, old automatics don't mix well with fresh engines. Same goes for cooling; it's less expensive to put a new radiator, heater core, and hoses on now instead of waiting till you new engine gets fried out on the highway.

Bogie  

I thought about a 350 but I have an excellent condition LG4 305 (from a caprice wagon) with relatively low miles. My plan at the moment is to use it as my projects short block and bolt on new cam/heads etc. This way I avoid the machine shop, get some hands on experience and save some cash.

Does this sound reasonable? Or would you recommend a different stragety for my first rebuild?  

you have everything there,sounds like a good combo,good luck with it  

Sounds good to me, nothing wrong with a good used engine as a starting point.

The 305 is very valve limited, a set of Vortec heads will wake it up. You've got to be a little careful when putting them on the 305, the valves are as big as you can stuff in there so the occasional slight machining variations can get them a little close to the bore walls. So you need to do a trial assembly, best with crank and pistons out, so you can check the fit. Offset dowel pins are avaliable that allow you to move the head around a bit to insure proper alignment and clearances.

Bogie  

Square 1
I found that the LG4 I have has a 8.6:1 compression ratio. I could run it asis but if I were to crank that up to 9.0:1 like my current (L03) engine it would probably blow the crap out of my head gasket/rings  

At this point Id probbly be better off sourcing a (low mile) running 305/350 from a 93-95 Silverado that way I get the Vortec heads. Im looking to expand my search to other vehicles that use the same engine to increase my chances of a "hit". Lucky for me the 305 isnt "much" sought after so I should be able to snatch one up cheap, if I go that route.

Thanks for the advice on the clearance I do need to spend more time in shop/tech manuals. Hopefully I'll land a block with vortec heads so as to eliminate the guess work. The LG4 is still a solid engine, might throw it in if I get desperate.

Well, off to do my homework...