If you go to the bank and have all your numbers like stated above AND a predetermined amount and a plan to make sure the deal has a reserve, the bank is going to feel much better about getting paid.

: Provide him with the loan via cash on my LLC's balance sheet, i.e. a loan receivable on my balance sheet with loan documents coming on behalf of my company and record the interest income each tax year on From 1040 Schedule C; orProvide him with a personal loan via my own personal bank account, i.e. a loan receivable directly to me (not my LLC) and loan documents that require monthly payments to me (again, not my LLC) over a pre-determined loan term / amortization schedule, and keep track of interest income as it comes in for each tax yearI totally hold harmless anyone that provides "insight" and know that I should consult with legal / accounting experts to get a binding answer, but can anyone throw me a bone with their thoughts / views on what would be most intelligent from a tax perspective?

Most landlords would be looking to find a tenant 60 days out and would be prepared to wait a considerable time to find the right tenant.I would reject your 9 month applicant and continue to look for someone that does not have a predetermined length of stay in mind.

There are some cases where wholesalers will bring buyers to agents but those are special/ predetermined relationships. 

We have a predetermined pay schedule as long as the timelines are being kept up with the contract.2.)

Lenders will typically pay out in predetermined phases after certain parts of the construction have been completed and inspected.

In looking at them, it looks like PenFed pays the closing costs as long as the member (the borrower, i.e. me) doesn't pay off the loan in < 24 months.Also, there's this - since the loans are variable APR, there's a pre-determined floor, but the max could go AS HIGH AS 18%!!! 

We would at some point have to sign an agreement for all of this that would have a "buy out" date pre-determined.  

For both primary and investment loan they also wrap in the mortgage payment for a predetermined length of time, so if your fix and flip will take 6 months you will not have to make mortgage payments during that time period.

I anticipate that creating automated (or at least predetermined) systems to deal with foreseeable events (through education and trial and error) will be paramount to our keeping our REI from becoming too time consuming.