The first is the prayers to the saints
I think there are a couple issues with this one. First, are the saints awake or asleep after they die? And second, if they are indeed awake, would asking them to pray for us do any good? I think the tradition of the Church definitely speaks affirmatively on these two issues, but I also think that the Scripture shows that they are awake, and do indeed present the prayers of those who pray to them to God. I think that this is seen, for example, in Revelation:
"And when he had taken the book, the four beasts and four and twenty elders fell down before the Lamb, having every one of them harps, and golden vials full of odours, which are the prayers of saints." - Rev. 5:8
Who exactly the twenty four elders are is a matter of interpretation. What is relevant for this post is that, whoever they might be, they are alive in heaven, and have "the prayers of the saints" with them. This is the passage that I think speaks most plainly about all of this, though there are some other passages in Revelation which also speak of the saints being alive in heaven:
"And when he had opened the fifth seal, I saw under the altar the souls of them that were slain for the word of God, and for the testimony which they held: And they cried with a loud voice, saying, How long, O Lord, holy and true, dost thou not judge and avenge our blood on them that dwell on the earth? And white robes were given unto every one of them; and it was said unto them, that they should rest yet for a little season, until their fellowservants also and their brethren, that should be killed as they were, should be fulfilled." - Rev. 6:9-11
"After this I beheld, and, lo, a great multitude, which no man could number, of all nations, and kindreds, and people, and tongues, stood before the throne, and before the Lamb, clothed with white robes, and palms in their hands; And cried with a loud voice, saying, Salvation to our God which sitteth upon the throne, and unto the Lamb. And all the angels stood round about the throne, and about the elders and the four beasts, and fell before the throne on their faces, and worshipped God, Saying, Amen: Blessing, and glory, and wisdom, and thanksgiving, and honour, and power, and might, be unto our God for ever and ever. Amen. And one of the elders answered, saying unto me, What are these which are arrayed in white robes? and whence came they? And I said unto him, Sir, thou knowest. And he said to me, These are they which came out of great tribulation, and have washed their robes, and made them white in the blood of the Lamb. Therefore are they before the throne of God, and serve him day and night in his temple: and he that sitteth on the throne shall dwell among them." - Rev. 7:9-15
Notice that the saints are alive in heaven, and this is before the final judgment. They "serve him day and night in his temple," indicating that this is something that is an ongoing activity. Notice also that these saints in heaven can communicate with God, and God can communicate with them as well. And besides these examples, I think there are a few other examples indicating that the saints are alive and awake after death, including the time when Moses and Elijah appeared at the transfiguration (Matt. 17:1-9; Lk. 9:28-36), and also the "dream, a kind of vision" that was discussed in the deuterocanonical book of 2 Maccabees, where the (formerly) dead Onias and Jeremiah are seen as being alive and able to communicate (2 Macc. 15:11-16).
It is also important to remember that intercessory prayer is something practices by Christians (Col. 1:3; 4:12; 1 Thes. 1:2; Rom. 1:9; Eph. 1:16; etc.), we Orthodox just extend it to those in the "Church triumphant" in heaven. The Orthodox would thus take literally the words of the Gospel that: "God is not the God of the dead, but of the living." (Matt. 22:32)
It might also be helpful to note that the Angels also pray for us, since this is also a practice that the Orthodox engage in. One example of this is seen in Zechariah, when an angel of God intercedes before God for Jerusalem and Judah: "Then the angel of the Lord answered and said, O Lord of hosts, how long wilt thou not have mercy on Jerusalem and on the cities of Judah, against which thou hast had indignation these threescore and ten years?" (Zec. 1:12) There is also the passage in the deuterocanonical book of Tobit, where the Archangel Raphael clearly says that he prays to God for people:
"I can now tell you that when you, Tobit, and Sarah prayed, it was I who presented and read the record of your prayer before the Glory of the Lord; and I did the same thing when you used to bury the dead. When you did not hesitate to get up and leave your dinner in order to go and bury the dead, I was sent to put you to the test. At the same time, however, God commissioned me to heal you and your daughter-in-law Sarah. I am Raphael, one of the seven angels who enter and serve before the Glory of the Lord." - Tob. 12:12-15
I realise that a Protestant might not attach much weight to deuterocanonical books, but it at least shows that such ideas were held by the Jews of the time leading up to the coming of our Lord.
the second is the apparent "legality" of some things. One example, is fasting it seems really legalistic. Like you can't eat meat from this time till that time, unless it's on a feast day and then it's only fish. You can't eat dairy on certain days, except for on some festival that seemed to involve cheese. I'm really not trying to make light of the Orthodox traditions...at all. I just feel like I'm stuck between a rock and a hard place as I believe God did set up a physical church on earth, but did He really intend for it to invlove all the "rules and regulations"? I say this knowing well that I have been involved in "come as you are", "freestyle", God doesn't care how you worship just so you do "religion" for the last 20 years. It's just really hard to know what to believe anymore
This is, I think, a matter of perspective. Some people do take it to legalistic extremes, and Orthodoxy is very organized and regimented in how it has set up the fasts, so I can see how it could come off as being legalistic. I would first just say that, at it's core, the Orthodox are trying to follow the the Bible, since it mentions fasting as a practice done by the early Church (Matt. 6:17-18; 17:21; Acts 13:2-3; 14:23; 27:33; 1 Cor. 7:5) Past that, I would just say that this is a practice which is meant to be a private act (cf Matt. 6:17-18), and one that is for our spiritual benefit. If it becomes legalistic, then some of the benefit will surely be diminished.
As to why Orthodoxy is so exacting about when you do and don't fast, and what you fast from, that is just given as general guidance, as a way to help out people by giving them an already-made plan to follow. However, IMO it is not meant to be one-size-fits-all, because it is supposed to be done within the context of the Church, where you and a spiritual father or father confessor can work out what is best for you personally. Pregnancy, diabetes, being new to the faith, and tons of other factors can be taken into consideration when working out how you approach fasting. But again, if and when it is made into something legalistic, it is missing the point of it.