To the most part those that do Sub2 and have done them over a longer period of time Do not come on Bigger Pockets bragging about it.

Can you extend settlement in order to get approvals? 

Towards the end of November, we got professional photos up of the reno and used the 20% new listing promo and quickly got 3 bookings for December in a two week period. 

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.

Even if I have a claim every 10 years I will have saved $80k over that time period compared to the people who pay for better insurance.

@Jonathan Greene and @Mike Grudzien I agree but I was hoping to hear from some certified appraisers and if they would comp leased land versus owned land in an appraisal.Jonathan, you are guaranteed the land through the current lease period, but not guaranteed of a renewal.  

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

If you go with a conventional loan for the cash out refinance, seasoning periods are longer which draws out the process. 

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. 

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