First off, welcome to Biggerpockets! It appears you're at the beginning stages, so I highly recommend you start by reading some books and listening to podcasts to build a foundational understanding of how real estate investing works, what makes a good deal, the different types of investments, etc. Then you can use the forum to refine your understanding through Q&A.
What works best for me may not work best for you. STR is constantly turning over, which means I'm constantly looking at it, making repairs, buying new linens, replacing broken items, landscaping, etc. STR was shut down during the "pandemic" when nobody could travel and now it's going to lose reservations because flooding is shutting down Yellowstone, the main attraction to my area. My STR makes double what I could earn with a LTR but I bought it before the market went crazy. If it were on the market with today's prices, I wouldn't give it a second glance and the same holds true for every vacation market I've looked at (Florida, South Carolina, Tennessee, etc.). There are pros and cons to each option. You need to educate yourself on what those are and decide what will work best for your finances, your goals, your time, etc.
You can purchase multiple properties. You can purchase a LTR and a STR and a personal residence. All depends on your financing. There's nothing legally stopping you from doing this.
Here's some generic advise for anyone starting out. It may or may not apply.
1. Start with BiggerPockets Ultimate Beginners Guide (free). It will familiarize you with the basic terminology and benefits. Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turneror The Unofficial Guide to Real Estate Investing by Spencer Strauss.
2. Get your finances in order. Get rid of debt, build a budget, and save. The idea that you can build wealth without putting any money into it is a recipe for disaster and the sales pitch of gurus trying to steal your money. A wise investor will not try to get rich quick with shortcuts. If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing. Check out my personal favorite, Set For Life by Scott Trench , or The Total Money Makeover by Dave Ramsey.
3. As you read these books, watch the biggerpockets podcasts. This will help clarify and reinforce what you are reading. You can hear real-world examples of how others have built their investment portfolio and (hopefully) learn to avoid their mistakes.
4. Now you need to figure out how to find deals and pay for them. Again, the BiggerPockets store has some books for this or you can learn by watching podcasts, reading blogs, and interacting on the forum. There is a handy search bar in the upper right that makes it easy to find previous discussions, blogs, podcasts, and other resources. Biggerpockets also has a calculator you can use to analyze deals and I highly recommend you start this as soon as possible, even if you are not ready to buy. If you consistently analyze properties, it will be much easier to recognize a good deal when it shows up. Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice. It doesn't take long to learn how to spot a good deal.
5. Study the market. You can learn to do this on your own or get a rockstar REALTOR to lead the way. I highly recommend a well-qualified REALTOR that works with investors and knows how to best help you.
6. Jump in! Far too many get stuck in the "paralysis by analysis" stage, thinking they just don't know enough to get started. The truth is, you could read 100 books and still not know enough because certain things need to be learned through trial-and-error. You don't need to know everything to get started; you just need a foundation to build on and the rest will come through experience and then refining your education.
You can build a basic understanding of investing in 3-6 months. How long it takes to be financially ready is different for everyone. Once you're ready, create a goal (e.g. "I will buy at least one single-family home, duplex, triplex, or fourplex before the end of 2019") and then do it. Real estate investing is a pretty forgiving world and the average person can still make money even with some pretty big mistakes.
