There's some very strict parameters but pretty powerful when executed well.

Welcome, the best way to make it happen, is to find an opportunity and execute. 

I'm so used to dealing with sellers who have lived in the home and have a vested interest in getting the closing executed on time.

(I)(1) The terms "real estate broker," "real estate salesperson," "foreign real estate dealer," and "foreign real estate salesperson" do not include a person, partnership, association, limited liability company, limited liability partnership, or corporation, or the regular employees thereof, who perform any of the acts or transactions specified or comprehended in division (A) of this section, whether or not for, or with the intention, in expectation, or upon the promise of receiving or collecting a fee, commission, or other valuable consideration:(a) With reference to real estate situated in this state owned by such person, partnership, association, limited liability company, limited liability partnership, or corporation, or acquired on its own account in the regular course of, or as an incident to the management of the property and the investment in it;(b) As receiver or trustee in bankruptcy, as guardian, executor, administrator, trustee, assignee, commissioner, or any person doing the things mentioned in this section, under authority or appointment of, or incident to a proceeding in, any court, or as a bona fide public officer, or as executor, trustee, or other bona fide fiduciary under any trust agreement, deed of trust, will, or other instrument that has been executed in good faith creating a like bona fide fiduciary obligation;(c) As a public officer while performing the officer's official duties;(d) As an attorney at law in the performance of the attorney's duties;(e) As a person who engages in the brokering of the sale of business assets, not including the sale, lease, exchange, or assignment of any interest in real estate;(f) As a person who engages in the sale of manufactured homes as defined in division (C)(4) of section 3781.06 of the Revised Code, or of mobile homes as defined in division (O) of section 4501.01 of the Revised Code, provided the sale does not include the negotiation, sale, lease, exchange, or assignment of any interest in real estate;(g) As a person who engages in the sale of commercial real estate pursuant to the requirements of section 4735.022 of the Revised Code.(2) A person, partnership, association, limited liability company, limited liability partnership, or corporation exempt under division (I)(1)(a) of this section shall be limited by the legal interest in the real estate held by that person or entity to performing any of the acts or transactions specified in or comprehended by division (A) of this section.

Take a look at your strategy and niche, see what you're trying to do, identify how your two properties can enable that strategy, then execute.

The lender might want an executed lease on the properties to show you are renting them but this is totally allowable by Fannie/Freddie.  

We all know reading/studying is much different than actually executing.

If they had a plan first, and that first deal was executed according to that plan, they wouldn't be asking "what do do next". 

The house hacking is also a great idea so I think you should look over your options, figure out what works best, and simply execute.

Now, at the same time, any rental lasting longer than 31 days is NOT considered STR, so besides LTRs there are also options of executive rentals and things of that nature that are not year long leases, but still "short term" in the sense that they're only for a month or two.And to your last question, again from my understanding and someone else could also speak to this, a STR permit can be held in the name of an LLC (I believe).