355 multiple problems

well first off the engine is sbc 355 97 block 85 heads air gap intake manifold mild cam 9 to 1 compression and a 700 R4 tranny ... the problems are wont run for longer than 2 minutes at idle. the timing i think is off because A. i dont have a timing mark on the damper and B. i turn the engine over and then the starter wont turn it over eventually .. is this bad? i think the reason it wont idle for very long is because of the choke maybe? but i wanted you smart guys opinion. oh before i go any further the carb is a Q-jet. next problem is the tranny is slipping like crazy and i dont have overdrive!!! i just replaced the pump seals in it but other than that its original from 88. i've got an in-line fuel pressure regulator and its set at 5psi....plugs show a little rich... also the tranny has all the electronic stuff and obviously i have a carb now so the computer thats still in the truck is obviously freaking out.. is the reason the tranny acting up because of some sort of limp in mode ???
any and all suggestions will be much appreciated here!! this is my first build so im a new guy!

added side note... sorry for how long all this is! but the fuel pump is in the tank from the fuel injection so it still has the return line which i just blocked off with a plug... because ive found with it unplugged, it just doesnt get enoug fuel.. and still doesnt.. the regulator is set at 5 but it definitely aint no 5 psi!!! so any ideas to get more back pressure without putting in a new return line????? also ive been thinking about taking the regulator out and putting in some sort of valve that i can turn up or down myself because i tried the no regulator in line and i obviously had too much pressure.. so some ideas would be awesome!!!!

I am not sure I have answer to your questions....but.....I have found the best way to tackle a situation like this is one thing at a time.....

I would take one problem at a time and solve it and after you sort each problem out and see if it solves your issues with the engine.....

I would address the fuel issue and timing issue first.


Keep at it ,you will get it solved.

yeah.. thanks for the advice... i got the engine running.. the regulator i had was a peace of crap so now i got one thats doin the job 110% of the time.. now im lookin for a tranny... a 700 R4 to be exact! anyone know of one that i can get for under $$ 350 $$ ???

if you are using a factory fuel pump in the tank, I believe you should run a return line from your regulator. when I did my v8 s10, I used the factory pump with a carb. I was told something about it cthe returning fuel cooling the pump. It's easy, just get a reg with the extra ports. any regulator I've used was adjustable. the one summit reccomended to me was a mallory unit at like 85$. just my opinion on your fuel set up.good luck