I'm wondering about any potential regulations that might make this a more difficult process than I'm anticipating. 

Sonya, this is going to be insanely difficult.

Also @Andrew Syrios thank you for your opinion also, it´s pretty much helpful to have different opinions and perspectives, but still difficult to decide when someone it´s just beginning.  

I will say this is a difficult RE market and I can poke holes in most RE purchases at this time.  

Properties in flood zones are harder and more expensive to insure, which lowers their perceived value and makes them more difficult to sell.

Option 4: 20% down on 2 to 3 properties Also open to hear other ideas, I'm self employed so getting a lender can be a bit more difficult.

That may increase your cost or limit the coverage you can get.The Year that the following were updated (either partially or fully) would be good to know:- Heating systems- Roof- Plumbing- electricalSome companies will not write properties with systems that have not been updated.As long as you are living there, the proper policy for a 1-4 family is a "Homeowners" policy.

That will most probably be offset by an increase in new mortgage costs and increased rates. 

Only one was ever difficult. 

Below are a few areas and things to look for if you're exploring investing in an AirBnB on the Oregon Coast.Most notably, the heart of the Oregon Coast in Lincoln City STR permits will be more difficult to come by.