We will continue to buy in this market.

Depending on the way their company operates, you filing your property as an investment on your taxes may be considered an issue for them depending on how stringent they are.

Very different from a typical insurance company. 

I work with a lot of househackers and they're typically on the 12 month cycle, rinse and repeat.While the proposition of acquiring an investment property outside of your market in a "landlord friendly" state may sound appealing, i would recommend you stay local for now and househack another couple of properties over the next few years until you've got some more time / experience under your belt.you would need a management company to cover your property that is outside of your market which would not only take 8-10% of your gross it would also leave you a bit vulnerable to a property management company that you A.)know nothing about and B.)you won't have the experience or cashflow or proximity to deal with any headaches that may arise.i would recommend staying local and househacking your way along for now and then maybe hire a local property management company initially to work with your current/local properties to get a taste of what to expect if and when you begin investing outside of your market.

Hey Adam,I’ve been in the Tampa real estate game for 20 years as an investor and owner of a property management company.

Depending on the type of commercial you want to get into my suggestion is to go work for a company that does commercial real estate as learning from people who do it and getting paid at the same time is not a bad strategy 

Airbnb is a company so the only way to buy one would be to own stock in the company. 

I own a mortgage company, so I have my loan officers use this Fannie Mae income calculation tool for all business for self borrowers: https://singlefamily.fanniemae.com/applications-technology/income-calculator .

I’m an investor with properties in both Indianapolis and Kokomo, as well as the owner of a property management company overseeing numerous units in Indianapolis for out-of-state investors.

If you plan to invest in multiple states or require advanced asset protection, consult a CPA or attorney to explore options like a holding company structure.