Curious what direction I should go in on either a flip or STR
You will need a joint venture with someone who has a lot more money or access to loans to do either. $20,000 would not get you to where you want to go.
Depending on your family and life situation. Recommend you do a House or MFH hack. Buy a 5 bedroom 5 bath or similar combo; or a 2/3/4 apartment building and live in them. Basically you want to live for free and build up equity faster using other peoples money.
Check out financing, taxes at sales time, etc the benefits of these two options over Flip/STR.
If your near a military base or other governmental unit, check out BAH, and try to get them as your Hack renters.
@Anna Tankersley For the handy-types, fix-and-flips are great because you can perform the renovations yourself (or with little help). I prefer buy, rehab, rent, refinance and repeat strategy (BRRRR) because you get monthly cashflow, tax benefits, and if you're lucky-- you can benefit from appreciation (if the market is in your favor).
The bigger picture, however, is that $20K is not enough to cover typical down payments AND closing costs. $50K cash-in-hand minimum to start with, to acquire the property, cover closing costs, and possibly have some leftover to perform minor cosmetic renovations.