Loan Approval, Owning Multiple Properties, and Real Talk

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I'm hoping that someone sees this and can dive in with "real talk." I'm going to lay it out there, and as I'm learning through this initial start up process (and I'm a quick learner) that I'll be able to realistically figure out what we can do financially, what we can afford, what our realities might look like, and other pieces of sound advice. I've been reading Bigger Pockets for quite awhile but haven't seen someone ask the exact type of questions I'm wondering about, so I would appreciate the help of those of you who have gone before. 

I'm going to try and organize my questions in numbered order, so commenting on any or all of them would be super helpful. Thank you!

1) My husband and I are both educators. I don't have to say much more for you to understand that our salaries are not those of corporate execs or other similar jobs. We love what we do, but are hungering for more and other ways to maximize our earning potential. Many educators take on side jobs in the summer to supplement their income; we'd rather stay home with our family. I'd like to simply know: Can people making salaries within the 50k range own multiple investment properties, or is it much more challenging and more for those, "you have to have money to make money" types? 

2) We have about 100k in equity in our personal home. We're sitting around a 35% DTI right now. We have about $25,000 in reserves in the bank, though we'd prefer not to use that as a down payment because we're learning that banks are wanting about 6 months of mortgage payments in reserves, correct? My question for those of you who own multiple properties: If you take out conventional mortgages on your subsequent properties, how do you come up with the 20% needed for each down payment? Do you take out HELOCs on your previous properties? Make enough from rental income? Or do you just make enough in your day jobs to save and come up with the 20% required? Investing in our first rental property won't really be a problem for us if we find a property around the 100k mark, but it's trying to figure out how (realistically) we could (and how you all) fund your subsequent properties that I am most interested in.

3) What is the average or common path to financing that you as investors use most often to buy your properties? Have you accumulated a lot of weath so you can buy outright? Do you go the conventional mortgage route? Go for private investors? Work with investment partners? I'm really just wondering whether two teachers who make around 50k a year each can own multiple rental properties. Do banks count your DTI on all of your properties and add them up together? How can so many of you own multiple investment properties?

4) What is the realistic "start up" cost for securing each and every investment property? I'm reading a lot about hiring real estate attorneys, creating LLCs for each property owned, working with real estate agents, making repairs, etc. If you were to take a 100,000 property as a baseline, how much would you expect to bring (out of pocket) to each home at closing based on the consultations you have, etc.?

5) How did each of you get started in investing? Did you have no money? Come into a windfall/inheritance? Save your own money? Have a well-paying job that funded it? I'd love to hear your stories. 

6) And finally... how many of you own properties in other states and how did you decide on those cities and states to invest in? We live on the west coast where property values are astronomical and rental rates are stagnant and soft. Most people won't pay more than $2000 in rent for a prime property in the city, and yet city real estate prices are through the roof. There are virtually ZERO rental properties within 100,000. Because of this, I feel like there is no way we can invest in our state because we do not have the 40,000 - 60,000 needed as a down payment for a 250-300k SFH property that our state is laden with. Incomes are not matching housing prices which is a huge issue, so Oregon is just not a great place for investing right now. We have family in the south and have been looking at South Carolina, Arkansas, Texas, North Carolina and Florida. What are the pros/cons and potential issues (besides having to for sure hire a property management company) to consider when investing in other states? Are there sales taxes assocaited? (we don't have them in Oregon).

Thank you SO much for any help on any of my questions you guys can offer-- transparency and realistic information is appreciated. I have a lot of experience in real estate as I mentioned, but there are some gaps I'm facing information-wise when it comes to getting started and then funding multiple investments on a public salary.