The lease dictates that "the Tenant shall not allow any other person, other than Tenant's immediate family or transient relatives and friends who are guests of the Tenant, to use or occupy the Premises without first obtaining LL's written consent."

I cant let tenants dictate how i run my business.

Don't let your immediate actions dictate your future... plan your future and make the decision to get you to where you want to go.

Experience with rehab (either flips or BRRRRs) can dictate the leverage, as well as your credit.  

Because if you are looking at 10 years down the road, wanting "X" in cash flow, or "X" in wealth, that will help dictate an answer as well. 

Replacement value (as shown by your insurance bid) is often in the 200's for a SF and sellers would be happy to ask that much for their properties, but neighborhood issues dictate a steep discount.

typically, contract law dictates that agreements for one year or more must be executed in writing. an email response is likely not enough to fulfill the requirements of an executed contract

If he is not licenced/insured, friend or not, you do not hire him.Precedents dictate proper professional management of your business.

Lease term does not dictate when a tennat will leave.I do not use term leases and have all tenants on M2M.

I am a cashflow investor so I don’t care so much where we are on the value of the property cycle, but I am strict on my cashflow needs which dictates the price I will pay.