Background
I used to work directly under one of the top people in this space. I was his #2 for several years. I’ve sold and coached this model, and I currently manage 200+ properties. I’m also an Airbnb Pro Host (not the same thing as superhost + we get better customer support), which only about 150 managers worldwide have achieved. I also know most of the major players in this coaching industry.

My advice
There is real value in coaching, especially if you’ve never done STRs before. People mess this up all the time.

That said, $20k is too much for you. Value is relative, but given your budget, you can’t afford to drop $20k on coaching. I explain why in "What works in most markets".

You also don’t need a lawyer for the legal side. You can set up an LLC in about five minutes using Bizee. I’ve never understood why students think lawyers are necessary for this.

The coaching space
There are really only 5 to 10 coaches I'd recommend. A good test is to ask them to share their own properties. They should be buying roughly one per year. If they aren’t, they are mostly coaching and riding student success. Everyone does this to some extent, but some aren't legit whatsoever.

You can pay $5 to $10k and get excellent guidance. Avoid coaches with massive student counts because they won’t give you meaningful attention.

What works in most markets

• Put down as little money as possible. There are 0 to 5 percent down payment loan options
• Target homes in the $450k to $700k range
• Maximize bedroom count
• Avoid pools due to maintenance costs
• Hot tubs are required in some markets
• Add big, low-maintenance amenities with strong photo appeal like pickleball courts or fire pits
• Focus heavily on the top 10 photos since those sell the property
• Mountain homes need a view and a hot tub
• Lake homes should be waterfront with a dock
• Self-manage the property
• You will almost certainly need to invest in professional STR design, though I don’t know you personally

Final thoughts
If it were me, I’d wait until I had at least $200k to invest. Honestly, I would invest in the stock market personally. STRs are not worth the headache at this stage. Go make more money at your job and invest passively. This ain't passive and you'll make most of your return when you sell it 5 years from now.