If you plan to use anyways, I would go with
2cc (400mg) deca/week for 10 weeks
1/2cc (100mg) prop eod or e3d until it runs out (or 13 weeks, which ever is sooner)
50mg winny/ed for weeks 1-4 and weeks 9-13.
Starting week 14, nolvadex @ 40mg/ed for 3 weeks.
You should not have any issues with gyno due to the low dose of test, but you may encounter some libido issues.
The deca could cause gyno, and if he is sensitive to estrogen, or aromatizes at a higher than normal level he may very well have a problem with gyno. Were looking at an average of 350mg test every week, and the test is of the propionate ester which can aromatize more than longer esters. Always be on the look out for gyno unless you want it. PCT should be started 2 weeks after last administration of the test, so if you run through week 13 take week 14 and 15 off and start PCT at the beginning of week 16.
Another thing you may want to consider with this cycle is your test/deca ratio is off. A rule of thumb to avoid problems is a 2:1 ratio of test to deca. I think you need to put off the cycle until you get in shape, or at least until you get back to training regularly. I think you should get your hands on some more test and up the test dosage and run a simple beginner test cycle. Here is what I would recommend for a first timer:
Week 1-14 500iu HCG 2x ew or e3d Stopping 4 days prior to PCT with last two shots of HCG @ 1500IU
Week 1-10 250mg deca ew
Week 1-12 500mg test ew
I dont think you need the winny at this point in your cycle history. Nothing wrong with saving it for future cycles. Slow and steady wins the race in this game. Get used to the drugs you'll be putting in your body and make sure you can handle them before you just start throwing everything but the kitchen sink. You might want to run some dbol with this cycle, but that is a personal choice. I am assuming that you have never cycled before in writing this from the sound of your OP.
PCT starting 2 full weeks after last admin of test.
What do you have available for PCT?