@Christopher V.
I am painfully introverted as well. And you are right, in the end it all comes down to that.
A good question to start asking yourself is "What is the absolute worst that could happen?" Then think it out in painstaking detail. Then think, "If the worst happens, how is it going to affect me permanently on a scale of 1 to 10". 10 being something that permanently scars you for life and is impossible to recover from. Almost everything is usually a 1. Remember, whatever you are most afraid of right now is likely what you need to do the most.
If you haven't read "How to win friends and influence people" by Dale Carnegie go on amazon right now and order it.
You mentioned starting an LLC several times throughout the post. Starting an LLC is very easy and can be done by other people for you. Don't get caught up with legal issues right now because you don't have much for anyone to take from you and you don't need an LLC to do your first deal. You don't have a lot of money to take so no one is going to be suing you.
Right now you should forget about everything that isn't going to make you money in the next 60 days. If you don't you are going to get caught up in the minutiae and trivial details that suck your focus, energy, and motivation (like the legal structure of an LLC). Since you are introverted you need to deal with this aggressively, if you don't you will spend 2 weeks working on your website, and you haven't talked to one seller or made any offers. Ask me how I know. You are a web developer so it might be even worse!!!!
Also, you sound like you are good with people and self deprecation is a great way to make people like you, thats one of the reasons Ben Franklin was so good with people. The best part of it is, when you meet with a seller and talk with them on the phone you will do about 5% of the talking, the rest should be active listening and focused attention.
I am 22, I have never had anyone laugh at me or even think I was that young. People usually think that I am 35 (trust me, I don't look 35). My hypothesis on this is that people are not expecting a young person so they subconsciously see you as being older than you are. Also, If you show competence and confidence, it doesn't really matter how old you are.
About the market. I don't know salem at all. Portland has low inventory and is highly competitive. I would say that compared to markets around the country the northwest is very difficult. But that doesn't really matter and should not be used for an excuse unless you are seriously considering moving to an "easy market". Forget about the market...there are deals everywhere. Worry about the market when you are established. Remember, forget about the minutiae, cut the fat.
Consider making the drive up to Portland for the Rarebird Investor Network on Monday at 6:30pm. Its free for you to check out the first couple times. You need to get involved with other investors.
If I was teaching myself from where you are now the first thing I would do is prescribe this solution. Make yourself uncomfortable.
Being an introvert is not bad, I think that is it good. It makes you a better listener. You just need to know when to control it.
Here my proposition:
Go to a mall and ask people, "Excuse me, I really like your shirt (or hat). Would you give it to me? I would be extremely grateful" (don't ask women for their shirt)
What's the worst that could happen? You get super nervous for the first 10 people and they tell you no and give you disgusted looks, 1 person tells a security guard and he confronts you, you ask him for his shirt, he says no and asks you to stop. You go to the other side of the mall and ask more people. Now its easier and you feel more confident with it. I guarantee you will get someones shirt or jacket.
Go do this tomorrow and come to the Rarebird Investor Network on Monday to tell me how it went.
A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have and the quality of life is also related to the quality of your questions.
What is the absolute worst that could happen?
If the worst happens, how is it going to affect me permanently on a scale of 1 to 10?
What scares me the most?
Is this going to make me money within 60 days?
What don't I know?
The list goes on