I have spent some time trying to get my 300d running good. I recently adjusted the valves and set the pump timing. Cleaned the fuel tank and replaced the filters. When i started it in the garage it ran good, but smokey. Took it down the road and it died a block away. Hooked up an inline pump and got it home but died shortly after. This has happened everytime i got the car started. It has two newer injectors. Does this sound like an air leak? Whats the next best step to take?

If that was another fuel supply pump you hooked up in the part highlighted in red makes it sounld like you have a fuel supply issue.

An air leak could cause a fuel supply issue. Could be the stock Fuel Supply/Lift Pump and or the Fuel Pressure Relief/Overflow Valve.

What color was the smoke and did the smoke smell like fuel or oil burning?

Wouldn't hurt to re-check the valve adjustment.

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84 300D, 82 Volvo 244Gl Diesel

Definitely smells of unburned fuel. Yes i hooked up an aftermarket inline pump. When the car died i had my girlfriend pump the primer and it would run until she stopped pumping. The lift pump seems to work fine, doesn't leak. Where is the bypass valve?
I will recheck the valves when i get time.

The bypass valve looked good, ball was seated. Although tthe valve was a bit rusty. Also a lot of pressure (mostly air) came out. I'm thinking I'll hook clear lines to a fuel can and see what happens

How's your air filter looking?

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1978 300D, 373,000km 617.912, 711.113 5 speed, 7.5mm superpump, HX30W turbo...many, many years in the making....
1977 280> 300D - 500,000km+ (to be sold...)
1984 240TD>300TD 121,000 miles, *gone*
1977 250 parts car
1988 Toyota Corona 2.0D *gone*
1975 FJ45>HJ45
1981 200>240D (to be sold...)
1999 Hyundai Lantra 1.6 *gone*
1980s Lansing Bagnall FOER 5.2 Forklift (the Mk2 engine hoist)
2001 Holden Rodeo 4JB1T 2WD

Air filter is newish. I got the car to start and stay running now, using a fuel can. It runs rough so i think i should do a compression test.

Remember to check the valve clearances before the compression test. That's if you have not already. You saw some rust in the relief valve? You may have a piston stuck at the top of its stroke in the injection pump if the car sat around a lot before you got it. Do the other things first.

One of the issues with cars from the snow belt is under car rust. The fuel line is steel & subject to rust. The latest roadway de-icing technique of using a beet juice brine mix on the roads has caused some issues with steel lines held to the floor pan &/or frame. It seems to seep into the space between the clamp and the line causing pin holes. I have a w126 in the shop with a similar fuel delivery issue. The lines are pin-holed at every clamp. The car limped in using an electric pump between the tank & first filter. (sound familiar?) I would still check out the remainder of the fuel system for rusty bits & injector/injection pump issues (re-check the valve adjustment, too). It sure sounds like you have a fuel delivery issue.