Ok, so this is the first time on a serious play through that I have decided to build a hearthfire house, the only problem for me is picking a steward.

My first question is- do I even need a steward?, and what will I miss out on if I don't get one?

I also would like recommendations for a steward. Keep in mind I am roleplaying.
-he/she needs to be someone my character can trust, and someone that my character would actually come into contact with.

I am a nightingale, and lord of the volkihar vampires. I am not doing the main quest either.

Edit: also I was going the housecarl for winstad (my house) but I heard he was glitched and would instead head for lakeveiw

Well you should make a thrives guild person as your steward

If you want to hire a carriage or a bard, or buy horses and other animals for your house, you have to hire a steward. There is no other way to get these things. Stewards can also furnish and decorate rooms in your house if you don't want to bother scrounging up the materials and building it all yourself. However, they will eventually add all furniture and decorations available for any room you have them furnish. They can also buy lumber and other building materials for you if you don't want to mess with mining it yourself or visiting the sawmills.

For roleplaying purposes, if you adopt kids but don't marry, the steward will be there to watch over your kids when you leave to do other stuff. You can also ask them to follow you at any time. One thing about stewards, though, is that once you hire them, it's a job for life. The only way to replace them with someone else is to have them die. Also, a steward can only provide services at one house, the one you hired him/her at first. You cannot change the home they're steward of.

As to who to hire, the NPCs available for hire as stewards are available as followers, but not all followers in the game can become stewards. The wiki has a page listing everyone in game you can hire as a steward. I usually pick the housecarls that come with the homes to be my stewards.

Not possible as none of them can be a follower.

Hmm I thought one of them could become a follower

I was planning on using the mortal housecarl, but I saw on the wiki that there was a glitch were he would head to lake view instead of windstad

Use the riften housecarl

I thought this was a great idea, but guess what. Wujeeta, the argonian that gives you the skooma quest, died when I was about level ten. I didn't think it was a big deal, I didn't remember her. Well it's a big deal now.

I can't become than of riften without that quest, which is bull crap.

If your on pc just go into console and use the resurrect command

I will use benor most likely.

Edit: never mind, it doesn't work.

If only

So, you're not on PC, then, I'm guessing. Have you done Illia's http://www.uesp.net/wiki/Skyrim:Repentance yet? If you're not inclined to use her as a follower, she makes a pretty good steward. In fact, due to the glitch she has of not being able to be reacquired after dismissing her, she's a lot less problematic as a steward than as a follower--at least, if you're not on PC (where her glitch can be corrected).