We do mostly retail, some behavioral health, hotel, apartment building, etc...

I recommend it for any new investor (or seasoned investor) :)I also have a full-time bartending gig at a large hotel in my town, so I assure you it is a balance game finding a way to make this happen every day.

I want to invest in hotels.

1)I don't want guests who regard our condo as a quasi-hotel.

However, I have a very strong feeling that Annapolis would be a great place to have a full time Airbnb rental, as three out of the four seasons there is always something going on and there never seem to be enough hotel rooms available. 

Should I rent a hotel, rent a place (monthly) or other?

I like the corporate lodging site mentioned and will also look into that.In terms of Hawaii regulations, to legally do a short-term rental you would need a non-conform use license, which hasn't been issued since the 80's (you can thank greedy hotel lobbyists for that).

I never thought $10k a month in income wouldn't entice me.If I knew I needed $500k down payment to purchase a motel/hotel or apt bldg that would product huge cash flow which is more secure than my current venture.

Hey Christopher, I figured it might be a set up for a guru meeting at a hotel or something.

I am interested in multifamily apartment buildings 8-30 units, small shopping centers/strip malls and small hotels.