I'd love to get info/opinions on whether there is a "standard" amount of time to increase rents in the Bay Area for Single Family Homes.How do property management companies/landlords handle rent increases for existing renters? 

Ask yourself this, if someone offered to handle all of the property maintenance, watch the property, place the tenant, handle rent collections, deliver rent to your bank account every month, and deal with any inspections and nuisance issues and they were asking for like $30 to $40 per week would you pay that?

Software can't handle rent collection on late tenants, noise complaints, parking violations, unauthorized pets or people, maintenance coordination and supervision, inspections, and so much more.I don't advise anyone to invest in another state unless they have a solid PM lined up to handle the investment for them.  

Quote from @Carlos Handler: This is all great stuff!

Moving from a 3 handle rate to an almost 8% DSCR feels like defeat.

Quote from @Jake Handler: I would love to connect with people in Northern New Jersey that are utilizing the Medium Term Rental strategy locally; specifically furnished rooms that are being rented. 

Then the guest speaker started discussing some legal topics and I thought some of the advice was not great (since I handle real estate transactions on a small scale) so it turned me off a bit.

Not saying that attorneys are great, but your attorneys wouldn't be customarily called upon to handle real estate transactions. 

This sounds like someone who needs to either handle all of their own repairs and let you handle rents/leasing or they need to self manage. 

Also, QB standard account code need to be modified to handle real estate expenses and income.