Real Estate agent Alysa Bunting is a great contact in that area.

Here is some info: SF STR FAQAssuming the info is up-to-date, it must be your permanent residence (you must live at the property for a minimum 275 days a year), you can rent unhosted a max of 90 nights a year, you need a business license, and you need to pay the city $925 for a STR certificate.

Examples are Ilikai or Waikiki Beach in Waikiki, or Kuilima Estates in Turtle Bay.I'm happy to answer any questions you have, so please never hesitate to contact me.  

For more info on Cleveland you'll want to read The Ultimate Guide to Grading Cleveland Neighborhoods.

With the limited info, I would say #1 is your smartest option but there are a lot of variables missing.

Some facts/info you may already know but if not:1) You assume the loan from the servicing bank, meaning you will work directly with the servicing bank.You assume the loan amount, but still need to come up with the difference of the VA loan amount and the sales price, in your case 172K. 2) No one will finance the entire remaining 172K amount.

They also have a support ticket system and customer support contact number that sends you directly to a human being.

We might be able to help you but would need more info. 

Also, any guides, info, or direction would be awesome. 

Get your CRM up and running and keep in contact with everyone with content about the market, keeping in touch with past clients - just asking them how their house is, let them know that you were thinking of them when you drove past the house,  ask them if they made any improvements, etc.