Ask yourself: do I really have the knowledge of real estate principles, real estate law and real estate finance; the network of contacts; the experience both in business in general and real estate in particular; the time available; and the analytical ability to compete against FULL TIME EXPERIENCED PROFESSIONALS to be successful in a field where the failure rate is so astronomically high?  

Would your STR business even exist without Airbnb?  

Many people choose NOT to have this, because the administrator will then vet every investment you make to ensure you do not invalidate your IRA.Invalidating your IRA means that you've done a prohibited transaction and the entire account is then deemed as distributed to you.If you don't want checkbook control, then I recommend a plan administrator such as Equity Trust - www.trustetc.comIf you are sure that you're aware of all the rules around prohibited transactions and disqualified people (who you can and can't do business with), then a plan administrator like Sense Financial would be a good place to start talking.  

I made a similiar mistake in business, paying $1.1M upfront for promises and had no way to cut losses when those promises were not delivered on.

The majority of the business I do is buying small multi families and identifying the towns that are more favorable for investing. 

You can find qualified buyers that are small business owners, tradesmen, etc just have someone qualified to do prop underwriting be fore you sign the agreement. 

I am currently a student at Florida International University, studying International Business.

I typically don't comment on other's businesses unless I know from personal experience.

and they're difficult to do, because you're up against businesses that do nothing but flip and BRRRR, and here you come along wanting to do 1 home run right out of the gate. 

There are a handful of active agents here on BP in the Portland area (including my business partner and I) who would be good places to start.