I also have a cleaner that comes through to clean a couple of Sundays out of the month. 

And get this, the professional cleaner they hired for the rental office and amenity spaces on this project, thought it was real wood!

Work your markets and local regional banks to get better pricing and or cleaner assets.  

3.First one couldn't be bothered as it wasnt a beach rental.Second one stuck anyone with a pulse in, never got money, and we got continual demands for cleaners and repairs.Third stole $4k.

They worry about what kind of scuzzy messes got spilled on them from the previous tenant, did the carpet cleaner do a "good enough" job?

I think you are certainly doing the right thing by posting your questions/concerns on the site.Maybe I got taken to the cleaners on my first purchase but I did not get any of the requests that you mentioned above.  

It doesn't make sense to take hours and hours to do something like this when it can be done within 1 hour.This also makes it cleaner on your GL.

You won't pay I need it now homeowner prices.Or, you can buy out of state and get taken to the cleaners on almost every repair bill you pay for because you're the out-of-state rich dude buying up local property and nobody gives a dog turn on the sidewalk care about you. 

So that is an issue, but you could add a cleaner approach and entry even with gravel if you are careful.Tenant preferences are also relevant. 

I originally was going to look for the office with the most training available, but literally all the offices i have been to offer roughly the same amount of training according to the calendars they gave, so that has kinda confused me in regards to what next to look into...Right now the top 2 based on how i felt after talking to the brokers are Berkshire Hathaway and Florida Luxury Realty...Berkshire Hathaway from the beginning seemed like a more cleaner operation, since both offices i stopped into had that new home feeling and presented very professional.