Good stuff - you are pretty spot on - technically people max out under conventional loans at 10 - but oftentimes its with fewer properties as people run into hurdles before hitting 10, some of which you mention - wanting to diversify strategies, multifamilies, needing LLCs etc.I think you are on the right track for DSCR Loans - I always say that DSCR is really perfect for people in the 5-50 property range - typically conventional is the best fit with your first few, and then when ready to make the "jump" to scaling bigger and faster - DSCR is the best bet.

I have had luck in the past with my realtor pulling the listing for a week or two, freshing up the listing and relisting at the same rate and getting it rented quickly.  2.5 weeks doesn't seem un-reasonable to me. 

That ol' chestnut of "boarder income" can be an annoying hurdle to deal with conventional finaincing.

The only way around this hurdle that I am aware of is having the loan serviced.

Depends on the size of the house but that doesn't sound unreasonable.

Am I asking an unreasonable amount or am I selling myself short here?

This would only be the 2nd tenant I've had at my first rental property, which was my family's previous home, and I really, so I really don't want to put myself at risk of having to go through legal hurdles if there's issues with her, so I'm strongly considering looking for a new tenant.

The primary hurdle for investors is that most homes have appreciated significantly during the past 3- years and the difference in the current mortgage balance and purchase price is required as a cash down payment.

I have an airbnb and the numbers are WAY up this summer, also manage another clients airbnb and both running almost fully booked up this year maybe the registration hurdles have lowered supply. 

They are very unreasonable.