I think one of the biggest risks you face with Cash Out is interest rate risk.It's really difficult to predict where interest rates will be in a 2-5 year time period, so it can also be challenging to model out future mortgage rates.

I am not sure the Tenant is so friendly, my property manager deals with them.If you have a PM, they should answer this question for you and handle the process.You should notify the PM and update your PM Agreement, W-9, banking information, etc.

I am curious to get an update after you launch.

Rob just updated everything...here is the site he tells everyone to visit for STR cost seg.STR Cost Seg

There are several lenders that have a 3 month seasoning period, a few with no seasoning at all. 

Depending on how much you need to raise the rents to market, the other updates in the building that are needed, how quickly you can rent to market rents will all drive your decision.

Most of my cancellations were within the cancellation period and I charge a cancellation fee for my direct bookings.

Plus, as mentioned your risk exposure would be huge if you didn't have a contract in hand to lease, plus they won't want to lease from you, because they are a Sticky or capture tenant.Start small and Make Your Big Mistakes Early.For a minute i couldn't figure out what you where talking about, then I realized I hadn't updated my bio in 5 years.

Flippers always get frustrated waiting for the home occupant period to end on them.

As someone who has read Harry Potter, it seems the best way to get the attention of the landlord is to send a scary looking giant to their home residence with a kindly worded letter.More seriously, I was on the other side of the coin previously where my wife put the ads up under her accounts instead of mine, so I couldn't check them without getting on her phone and I was inundated with people looking to see the property (probably 50 over a 5 day period) and was trying to send semi-personalized notes to each one--and it all ended up being too much to handle and I ended up ghosting or not replying to many people after I found an applicant.