SO MUCH STRESS.

. This will be my first property so it would be nice to work in a solid buffer as far as cash flow goes to reduce the risk (or at least be compensated for the extra risk).

We STR owners need to stress to everyone - neighbors/City Govt/Etc that STRs are (almost) always in perfect condition.

When I first started I’d allow bookings pretty much back to back and it got stressful if I had meetings at work and a tight turnaround timeline.

It might not be the most popular suggestion, but I would rather spend some bucks and reduce headaches, not have an irate tenant for a few months, and greatly reduce a tenant from squatting/damaging the place on his/her way out.

My duties would be reducing vacancy, collecting rents, screening/choosing tenants, Maybe be paid on a 1099?

I would've like to make my case of being grandfathered in for the simple fact that the previous owner (whom is close to 80 years of age and self managed as Owner Occupied for over 35 years) had tried in the past:  1st - To reduce taxes because it's listed as a 3 & 2 but then the tax site has it as 6+ and when the old man had them visit the buildings they seen 7 mailboxes that USPS installed( so he decided to stay shut and not pursue it) 2nd- The 2 family already had 3 gas meters and even a fire escape because the 3rd floor studio apartment only has access thru back door.The front building has 4 gas meters, 1st floor, 2nd floor, 3rd floor and one for the front Studio apartment (which is like a basement apartment) but its street level with main entrance off sidewalk. 

Likely to be higher priced and with reduced coverage.

If you don't have something structured where you can keep everyone is a seat for 30 to 45 minutes then you may as well just smoke some joints, drink beer and whiskey and have a wild party nobody will forget.One meeting could be for flipping, single family investing, multi-family investing, the best ways to find properties, how to do rehabbing, how to deal with contractors, how to do the math for single family and multi-family investing before and after the purchase, financing, dealing with commercial investments, how to do accounting and reduce taxes, how to streamline your entire operation, what software to use and how to use it and a lot more.Most meetings have only coffee, water and cookies for people to munch on and not much more.

Of course I'd have to analyze specific properties to determine if this would make sense, but I just don't know if I'm crazy to consider selling a payed-off, cash flowing house to take on 2-3 mortgages (and reduced cash flow).